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. Author manuscript; available in PMC: 2014 Sep 9.
Published in final edited form as: Tetrahedron. 2013 Sep 9;69(36):7719–7731. doi: 10.1016/j.tet.2013.04.127

Table 1.

Conversion of thioureas (8a, R = CH3; 8b, R = (CH2)2Ph; 8c, R = CH(CH3)2) to thioimidates 9a-c and 2-aminopyrimidines 10a-c according to Scheme 2.

Entry 8/Conditions 9/Additive/Time 10/Yield %a
1 8a/MeOTf, THF, 1.5 h 9a/NH4OAc/20 h 10a/77
2 8a/MeOTf, ClCH2CH2Cl, 0.75 h 9a/NH4OAc/15 h 10a/30
3 8a/MeOTf, PhCl, 3.5 h 9a/NH4OAc/17 h 10a/61
4 8a/MeOTf, PhCl, 15 h 9a/NH4Cl/21 h 10a/51
5 8a/(MeO)2SO2, THF, 60 h 9a/NH4OAc/17 h 10a/57
6 8b/MeOTf, PhCl, 3.5 h 9b/NH4OAc/17 h 10b/39
7 8c/MeOTf, PhCl, 3.5 h 9c/NH4OAc/20 h 10c/33
a

Isolated yield of purified product.