3-Chloroaniline → HCID 71738748, compound

HRID 63155Notes

Reaction equation

HRID 63155 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.[Cl:23][C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1>>[Cl:23][C:24]1[CH:25]=[C:26]([NH:30][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)[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 79323-ChloroanilineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738748HCID 71738748, 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 (3-chlorophenyl)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, DMSO-d6) δ ppm 2.03 (s, 3H), 2.20 (s, 3H), 4.51 (d, J=3.0 Hz, 2H), 6.91 (d, J=6.8 Hz, 1H), 7.02-7.15 (m, 2H), 7.20 (t, J=6.4 Hz, 1H), 7.26 (d, J=8.1 Hz, 1H), 7.55 (bs, 1H), 7.69 (t, J=7.9 Hz, 1H), 7.78 (s, 1H), 8.10 (s, 1H), 8.49 (d, J=3.8 Hz, 1H); MS (ESI) m/z 340.1 (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-3b3b67f4e9aa4a14b360f8c51e0dd3ed
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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