4-Fluorobenzylamine → HCID 71737958, compound

HRID 63185Notes

Reaction equation

HRID 63185 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:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][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:26][CH:25]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71737958HCID 71737958, 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 (4-fluorobenzyl)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, CDCl3) δ ppm 1.92 (s, 3H), 2.27 (s, 3H), 4.56 (d, J=3.8 Hz, 2H), 4.72 (d, J=2.8 Hz, 2H), 4.78 (bs, 1H), 5.70 (bs, 1H), 6.94 (t, J=8.6 Hz, 2H), 7.13 (d, J=7.8 Hz, 1H), 7.20 (t, J=7.5 Hz, 2H), 7.29 (bs, 1H), 7.57 (t, J=7.5 Hz, 1H), 8.57 (d, J=3.2 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-5d64c5f89a8f4f34b28697c973085b34
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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