(4-Chloropyridin-2-yl)methanamine → N2-[(4-chloropyridin-2-yl)methyl]-N4-cyclohexyl-5,6-dimethylpyrimidine-2,4-diamine

HRID 63117Notes

Reaction equation

HRID 63117 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]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:25]C1C=CN=C(CN)C=1>>[Cl:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:18][NH:17][C:11]2[N:10]=[C:9]([NH:8][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=2)[CH:24]=1

Participants

3

Reactant 2

HCID 22727148(4-Chloropyridin-2-yl)methanamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738408N2-[(4-chloropyridin-2-yl)methyl]-N4-cyclohexyl-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-chloropyridin-2-yl)methyl]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, methanol-d4) δ ppm 1.16-1.28 (m, 5H), 1.55-1.75 (m, 5H), 1.96 (s, 3H), 2.32 (s, 3H), 3.80 (s, 1H), 4.70 (s, 2H), 7.39 (d, J=3.76 Hz, 1H), 7.48 (s, 1H), 8.46 (d, J=5.10 Hz, 1H); MS (ESI) m/z 346.0, 348.1 (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-84ead79e5e654dd292ebd241e053c53f
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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