(4-Ethylpyridin-2-yl)methanamine → N4-(4,4-difluorocyclohexyl)-N2-[(4-ethylpyridin-2-yl)methyl]-5,6-dimethylpyrimidine-2,4-diamine

HRID 63179Notes

Reaction equation

HRID 63179 reaction equation
Cl.C1(NC2C(C)=C(C)N=C(NCC3C=CC=CN=3)N=2)CCCCC1.[CH2:25]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][NH2:34])[CH:28]=1)[CH3:26].Cl[C:36]1[N:41]=[C:40]([NH:42][CH:43]2[CH2:48][CH2:47][C:46]([F:50])([F:49])[CH2:45][CH2:44]2)[C:39]([CH3:51])=[C:38]([CH3:52])[N:37]=1>>[F:50][C:46]1([F:49])[CH2:47][CH2:48][CH:43]([NH:42][C:40]2[C:39]([CH3:51])=[C:38]([CH3:52])[N:37]=[C:36]([NH:34][CH2:33][C:29]3[CH:28]=[C:27]([CH2:25][CH3:26])[CH:32]=[CH:31][N:30]=3)[N:41]=2)[CH2:44][CH2:45]1

Participants

4

Reactant 3

HCID 18340919(4-Ethylpyridin-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 71738979N4-(4,4-difluorocyclohexyl)-N2-[(4-ethylpyridin-2-yl)methyl]-5,6-dimethylpyrimidine-2,4-diamine

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-ethylpyridin-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 as the hydrochloride salt as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.59 Hz, 3H), 1.57-1.1.89 (m, 11H) 2.25 (s, 3H) 2.62 (m, 2H) 3.95 (s, 1H) 4.64 (d, J=5.12 Hz, 2H) 7.17 (d, J=5.12 Hz, 1H) 7.24 (s, 1H) 7.64 (d, J=6.40 Hz, 1H) 8.31 (s, 1H) 8.40 (d, J=4.94 Hz, 1H) 12.58 (bs, 1H); MS (ESI) m/z 375.9 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-606d71fb731f436f92e772a61ee54974
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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