4-Methoxybenzylamine → N4-cyclohexyl-N2-(4-methoxybenzyl)-5,6-dimethylpyrimidine-2,4-diamine

HRID 63099Notes

Reaction equation

HRID 63099 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](NCC3C=CC=CN=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:32][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738263N4-cyclohexyl-N2-(4-methoxybenzyl)-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-methoxybenzyl)amine instead of (pyridin-2-ylmethyl)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 white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10-1.13 (m, 1H), 1.24-1.35 (m, 3H), 1.62 (d, J=13.16 Hz, 1H), 1.72 (d, J=9.94 Hz, 4H), 1.87 (s, 3H), 2.22 (s, 3H), 3.72 (s, 3H), 3.94 (s, 1H), 4.46 (d, J=5.37 Hz, 2H), 6.88 (s, 2H), 7.26 (s, 2H), 7.57 (s, 1H), 8.01 (s, 1H), 12.66 (bs, 1H); MS (ESI) m/z 341.7 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe product was purified by column chromatography
  3. washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
  4. washthe final product was washed with diethyl ether

Sources & evidence

ORD record
ord-e0eb8a6576354cb6a497515db4339b65
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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