2-chloro-5-ethyl-N-(4-fluorophenyl)-6-methylpyrimidin-4-amine → 5-ethyl-N4-(4-fluorophenyl)-6-methyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
Reaction equation
Cl.C1(NC2C(C)=C(C)N=C([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)N=2)CCCCC1.Cl[C:26]1[N:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:29]([CH2:40][CH3:41])=[C:28]([CH3:42])[N:27]=1>>[CH2:40]([C:29]1[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[N:31][C:26]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:27][C:28]=1[CH3:42])[CH3:41]Participants
Procedure
The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using 2-chloro-5-ethyl-N-(4-fluorophenyl)-6-methylpyrimidin-4-amine (Step A) instead of 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine. The product was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a light-grey solid. 1H NMR (300 MHz, methanol-d4) δ ppm 1.09-1.20 (m, 3H), 2.25-2.35 (m, 3H), 2.52-2.62 (m, 2H), 4.57 (bs, 2H), 6.80-6.88 (m, 2H), 7.20-7.36 (m, 4H) 7.65-7.76 (m, 1H) 8.50 (bm, 1H); MS (ESI) m/z 338.8 (M+1)+.
Workup
- customThe titled compound was synthesized
- customThe product was purified by column chromatography
- washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
- washthe final product was washed with diethyl ether
Sources & evidence
- ORD record
- ord-c66d021d38a24c5b85077c36b113b501
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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