(1-methyl-1H-imidazol-4-yl)methanamine → N4-cyclohexyl-5,6-dimethyl-N2-[(1-methyl-1H-imidazol-4-yl)methyl]pyrimidine-2,4-diamine

HRID 63114Notes

Reaction equation

HRID 63114 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[CH:24]=CC=[CH:21][N:20]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:25][N:26]1C=C(CN)N=C1>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[N:20]=[CH:21][N:26]([CH3:25])[CH:24]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 2795114(1-methyl-1H-imidazol-4-yl)methanamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738405N4-cyclohexyl-5,6-dimethyl-N2-[(1-methyl-1H-imidazol-4-yl)methyl]pyrimidine-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 [(1-methyl-1H-imidazol-4-yl)methyl]amine instead of (pyridin-2-ylmethyl)amine. The 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, methanol-d4) δ ppm 1.25-1.38 (m, 5H), 1.70-1.85 (m, 5H), 1.97 (s, 3H), 2.30 (s, 3H) 2.71 (s, 1H), 3.72 (s, 3H), 4.08 (s, 1H), 4.53 (s, 2H), 7.07 (s, 1H), 7.72 (s, 1H); MS m/z 315.7 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-88c2abb81538492ca3a99c515e0d0cce
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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