(4-Methylpyridin-2-yl)methanamine → N4-(4,4-difluorocyclohexyl)-5,6-dimethyl-N2-[(4-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamine

HRID 63119Notes

Reaction equation

HRID 63119 reaction equation
Cl.C1(NC2C(C)=C(C)N=C(NCC3C=CC=CN=3)N=2)CCCCC1.[CH3:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32][NH2:33])[CH:27]=1.Cl[C:35]1[N:40]=[C:39]([NH:41][CH:42]2[CH2:47][CH2:46][C:45]([F:49])([F:48])[CH2:44][CH2:43]2)[C:38]([CH3:50])=[C:37]([CH3:51])[N:36]=1>>[F:49][C:45]1([F:48])[CH2:46][CH2:47][CH:42]([NH:41][C:39]2[C:38]([CH3:50])=[C:37]([CH3:51])[N:36]=[C:35]([NH:33][CH2:32][C:28]3[CH:27]=[C:26]([CH3:25])[CH:31]=[CH:30][N:29]=3)[N:40]=2)[CH2:43][CH2:44]1

Participants

4

Reactant 3

HCID 15144432(4-Methylpyridin-2-yl)methanamineHCID 1178176732-Chloro-N-(4,4-difluorocyclohexyl)-5,6-dimethylpyrimidin-4-amineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738409N4-(4,4-difluorocyclohexyl)-5,6-dimethyl-N2-[(4-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamineYield 45%

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 [(4-methylpyridin-2-yl)methyl]amine instead of (pyridin-2-ylmethyl)amine and 2-chloro-N-(4,4-difluorocyclohexyl)-5,6-dimethylpyrimidin-4-amine (Step A) instead of 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine. The product was purified by crystallization from ethanol to afford the titled compound (45% yield) as the hydrochloride salt as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.45-1.55 (m, 4H), 1.80-2.05 (m, 7H), 2.28 (s, 3H), 2.52 (s, 3H), 4.05 (bs, 1H), 4.99 (d, J=5.37 Hz, 2H), 7.65-7.78 (m, 3H) 8.31 (s, 1H), 8.67 (d, J=5.91 Hz, 1H), 13.42 (s, 1H); MS (ESI) m/z 362.4 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe product was purified by crystallization from ethanol

Sources & evidence

ORD record
ord-1c7361a93c3646769703d6bea06bb172
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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