2-Fluoro-6-methylaniline → N4-(2-fluoro-6-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63162Notes

Reaction equation

HRID 63162 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]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH2:31]>>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH:31][C:7]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:8]=1

Participants

3

Reactant 2

HCID 141554112-Fluoro-6-methylanilineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738800N4-(2-fluoro-6-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)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 (2-fluoro-6-methylphenyl)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 white solid. 1H NMR (300 MHz, methanol-d4) δ ppm 2.07 (s, 3H), 2.11 (s, 3H), 2.23 (s, 3H), 4.29 (s, 2H), 6.88 (t, J=9.1 Hz, 1H), 6.97 (t, J=5.9 Hz, 2H), 7.13 (m, 1H), 7.26 (t, J=7.3 Hz, 1H), 7.61 (t, J=7.3 Hz, 1H), 8.34 (d, J=5.0 Hz, 1H); MS (ESI) m/z 338.8 (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-77e66745da6e4057a6d37f3d87676b68
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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