N-[5-(Di­phenyl­phosphorylmeth­yl)-4-(4-fluoro­phen­yl)-6-iso­propyl­pyrimi­din-2-yl]-N-methyl­methane­sulfonamide

Ya-Ming Wu

doi:10.1107/S1600536813028286

. 2013 Oct 19;69(Pt 11):o1673. doi: 10.1107/S1600536813028286

N-[5-(Diphenylphosphorylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Ya-Ming Wu ^a,^*

PMCID: PMC3884331 PMID: 24454107

Abstract

In the title compound, C₂₈H₂₉FN₃O₃PS, the pyrimidine ring is oriented at a dihedral angle of 50.9 (2)° with respect to the florobenzene ring, while the two phenyl rings bonding to the same P atom are twisted with respect to each other, making a dihedral angle of 62.2 (2)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯F hydrogen bonds into a three-dimensional supramolecular architecture.

Related literature

For the synthesis of the title compound, an intermediate for the preparation of the statin rosuvastation {systematic name: (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid}, see: Brieden & Veith (2000 ▶). graphic file with name e-69-o1673-scheme1.jpg

Experimental

Crystal data

C₂₈H₂₉FN₃O₃PS
M _r = 537.57
Monoclinic,
a = 14.023 (3) Å
b = 6.3830 (13) Å
c = 30.493 (6) Å
β = 102.79 (3)°
V = 2661.7 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.957, T _max = 0.978
5109 measured reflections
4898 independent reflections
2568 reflections with I > 2σ(I)
R _int = 0.092
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.136
S = 1.00
4898 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028286/xu5743sup1.cif

e-69-o1673-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028286/xu5743Isup2.hkl

e-69-o1673-Isup2.hkl^{(239.9KB, hkl)}

Click here for additional data file.^{(9.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813028286/xu5743Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1ⁱ	0.96	2.56	3.363 (5)	141
C2—H2C⋯Fⁱⁱ	0.96	2.52	3.202 (6)	128
C13—H13A⋯O2ⁱⁱⁱ	0.93	2.53	3.350 (6)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The author thanks the Center of Testing and Analysis of Nanjing University for the data collection.

supplementary crystallographic information

1. Comment

The title compound is an intermediate for the preparation of rosuvastation (Brieden & Veith, 2000). We herein report its molecular and crystal structure (Fig. 1). The dihedral angles between the aromatic rings are: 30.7 (2)° (A/B), 65.76 (1)° (A/D), 50.9 (2)°(A/E), and 62.2 (2)° (B/D) [with the rings defined as: A =C3/N2/C4—C6/N3, B=C11—C16, D=C17—C22 and E=C23—C28]. In the crystal structure, no classic hydrogen bond was observed and molecules were stacked to form three-dimensional framework by weak C—H···O and C—H···F interactions (Table 1) (Fig. 2).

2. Experimental

The title compound was synthesized according to a procedure published by Brieden & Veith (2000). Colorless crystals suitable for X-ray analysis were obtained by dissolving the compound (0.5 g) in ethanol (80 ml) and evaporating the solvent slowly at room temperature for about 5 d.