4-Fluorobenzylamine → N4-cyclohexyl-N2-(4-fluorobenzyl)-5,6-dimethylpyrimidine-2,4-diamine

HRID 63100Notes

Reaction equation

HRID 63100 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.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[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][C:26]([F:25])=[CH:27][CH:28]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738264N4-cyclohexyl-N2-(4-fluorobenzyl)-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-fluorobenzyl)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 1.03-1.10 (m, 1H), 1.20-1.34 (m, 2H), 1.59 (s, 1H), 1.68 (t, J=12.22 Hz, 4H), 1.87 (s, 3H), 2.23 (s, 3H), 3.86 (d, J=8.87 Hz, 1H), 4.52 (d, J=5.37 Hz, 2H), 7.14 (t, J=8.60 Hz, 2H), 7.33-7.38 (m, 2H), 7.57 (d, J=7.52 Hz, 1H), 8.10 (s, 1H), 12.78 (bs, 1H); MS (ESI) m/z 329.2 (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-a62da2b091d0470baad433db2f5db95c
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

Loading…