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. 2017 Sep 22;22(10):1592. doi: 10.3390/molecules22101592

Table 1.

Synthesis of 2,4-diamino-5-aryl-6-substituted pyrimidine derivatives 16a-p via Suzuki reactions.

graphic file with name molecules-22-01592-i001.jpg

Entry R2 R3 Product Yield c (%) Clog P d
1 -CH2OCH3 (14a) 4-OCF3 16a a 74 2.99
2 -CH2OCH3 (14a) 3-OCF3 16b a 74 2.99
3 -CH2OCH3 (14a) 3-CH2OCH2CF3 16c a 70 2.29
4 -CH2OCH3 (14a) 3-CH3-5-CH3-4-SO2NHOCH3 16d a 73 1.19
5 -CH2OCH3 (14a) graphic file with name molecules-22-01592-i002.jpg 16e a 70 3.59
6 -CH2CH2OCH3 (14b) 4-OCF3 16f a 75 3.37
7 -CH2CH2OCH3 (14b) 3-OCF3 16g a 94 3.37
8 graphic file with name molecules-22-01592-i003.jpg (14c) 4-OCF3 16h a 87 2.81
9 graphic file with name molecules-22-01592-i003.jpg (14c) 3-OCF3 16i a 73 2.81
10 graphic file with name molecules-22-01592-i003.jpg (14c) 3-CH2OCH2CF3 16j a 91 2.11
11 graphic file with name molecules-22-01592-i003.jpg (14c) 3-CH3-5-CH3-4-SO2NHOCH3 16k a 72 1.01
12 graphic file with name molecules-22-01592-i003.jpg (14c) graphic file with name molecules-22-01592-i002.jpg 16l a 99 3.42
13 graphic file with name molecules-22-01592-i004.jpg (14d) 4-OCF3 16m a 91 3.56
14 graphic file with name molecules-22-01592-i004.jpg (14d) 3-OCF3 16n a 91 3.56
15 graphic file with name molecules-22-01592-i004.jpg (14d) 4-COOCH3 16o b 68 2.39
16 graphic file with name molecules-22-01592-i004.jpg (14d) 3-COOCH3 16p b 51 2.39

Reaction Conditions: a Pd(dbpf)Cl2 (0.02 mmol) and K2CO3 in EtOH/toluene/H2O at 90 °C for 24 h; b Pd(dbpf)Cl2 (0.02 mmol) and K2CO3 in THF/H2O at 70 °C for 20 h in sealed tube; c Isolated yields; d Calculated using ChemBioDraw (PerkinElmer, Waltham, MA, USA) 12.0.