(5-Methylpyridin-2-yl)methanamine → N4-cyclohexyl-5,6-dimethyl-N2-[(5-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamine

HRID 63173Notes

Reaction equation

HRID 63173 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:25]C1C=CC(CN)=NC=1>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 11423586(5-Methylpyridin-2-yl)methanamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738924N4-cyclohexyl-5,6-dimethyl-N2-[(5-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamine

Procedure

The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using [(5-methylpyridin-2-yl)methyl]amine instead of (pyridin-2-ylmethyl)amine. The product 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 0.97-1.33 (m, 5H), 1.51-1.69 (m, 5H), 1.87 (s, 3H), 2.24 (d, J=6.0 Hz, 6H), 3.73 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 7.20 (d, J=7.79 Hz, 1H), 7.56 (d, J=8.06 Hz, 2H), 8.06 (t, J=5.6 Hz, 1H), 8.33 (s, 1H), 12.90 (bs, 1H); MS (ESI) m/z 326.1 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe product 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-0853d179f8df4af09c1fb12f282ba4d2
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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