3-Methoxybenzylamine → N4-cyclohexyl-N2-(3-methoxybenzyl)-5,6-dimethylpyrimidine-2,4-diamine

HRID 63115Notes

Reaction equation

HRID 63115 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:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31]>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:31][CH2:30][C:29]3[CH:32]=[CH:33][CH:34]=[C:27]([O:26][CH3:25])[CH:28]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 211563-MethoxybenzylamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738406N4-cyclohexyl-N2-(3-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 (3-methoxybenzyl)amine instead of (pyridin-2-ylmethyl)amine. The crude product was purified by crystallization from ethanol (10 mL) to afford the titled compound as the hydrochloride salt as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.15-1.28 (m, 5H), 1.60-1.80 (m, 5H), 1.87 (s, 3H), 2.21 (s, 3H), 3.72 (s, 3H), 3.86 (s, 1H), 4.48 (d, J=5.64 Hz, 2H), 6.75-6.89 (m, 3H), 7.23 (t, J=7.93 Hz, 1H), 7.56 (d, J=7.52 Hz, 1H), 8.40-8.55 (m, J=38.95 Hz, 1H), 12.56 (s, 1H); MS (ESI) m/z 341.5 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude product was purified by crystallization from ethanol (10 mL)

Sources & evidence

ORD record
ord-71abcb7660ef4546a75db4f1847b2414
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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