Cyclohexanemethylamine → HCID 71738981, compound

HRID 63180Notes

Reaction equation

HRID 63180 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:23]1(CN)CCCC[CH2:24]1>>[CH:5]1([CH2:1][NH:6][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)[CH2:4][CH2:3][CH2:2][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 76688CyclohexanemethylamineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738981HCID 71738981, compound

Procedure

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using 1-cyclohexylmethanamine instead of cyclopentanamine. The crude material 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 0.66-0.73 (m, 2H), 1.00 (bs, 3H), 1.35 (bs, 1H), 1.42-1.58 (m, 5H), 1.86 (s, 3H), 2.18 (s, 3H), 3.06 (bs, 2H), 4.58 (bs, 2H), 7.26 (bs, 2H), 7.40-7.46 (m, 1H), 7.68-7.74 (m, 1H), 8.49 (bs, 1H); MS (ESI) m/z 326.5 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude material 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-e6b344e8baf94cde89b92e02e7a00291
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

Loading…