4-(Trifluoromethoxy)aniline → 5,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-[4-(trifluoromethoxy)phenyl]pyrimidine-2,4-diamine

HRID 63146

Reaction equation

HRID 63146 reaction equation
C1(N[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)CCCC1.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>>[CH3:13][C:12]1[C:7]([NH:32][C:29]2[CH:28]=[CH:27][C:26]([O:25][C:24]([F:33])([F:34])[F:23])=[CH:31][CH:30]=2)=[N:8][C:9]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:10][C:11]=1[CH3:14]

Participants

3

Reactant 2

HCID 6008484-(Trifluoromethoxy)anilineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 717386845,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-[4-(trifluoromethoxy)phenyl]pyrimidine-2,4-diamine

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 [4-(trifluoromethoxy)phenyl]amine 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 light-yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.07 (s, 3H), 2.34 (s, 3H), 4.70 (d, J=3.6 Hz, 2H), 5.92 (bs, 1H), 6.44 (bs, 1H), 7.01-7.21 (m, 3H), 7.16 (bs, 1H), 7.44-7.61 (m, 3H), 8.58 (bs, 1H); MS (ESI) m/z 390.7 (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-145835a0d5454b48921779e610f27c42
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

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