Cyclobutylamine → N4-cyclobutyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63137

Reaction equation

HRID 63137 reaction equation
[CH:1]1([NH:6][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)[CH2:5][CH2:4][CH2:3]C1.C1(N)CCC1>>[CH:1]1([NH:6][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)[CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738611N4-cyclobutyl-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 cyclobutanamine 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 (400 MHz, methanol-d4) δ ppm 1.60-1.68 (m, 2H), 1.83-1.96 (m, 5H), 2.108-2.15 (m, 2H), 2.20 (s, 3H), 4.26-4.32 (m, 1H), 4.62 (bs, 2H), 7.28 (t, J=6.4 Hz, 1H), 7.41 (d, J=8.1 Hz, 1H), 7.76 (t, J=5.9 Hz, 1H), 8.47 (d, J=4.4 Hz, 1H); MS (ESI) m/z 284.2 (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-6dc5b369389b4dd09e51b76bd2ad308d
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

Loading…