(2-Thienylmethyl)amine → N4-cyclohexyl-5,6-dimethyl-N2-(2-thienylmethyl)pyrimidine-2,4-diamine

HRID 63113Notes

Reaction equation

HRID 63113 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]=CN=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[S:25]1C=CC=C1CN>>[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[S:25][CH:22]=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 34005(2-Thienylmethyl)amineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738403N4-cyclohexyl-5,6-dimethyl-N2-(2-thienylmethyl)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 (2-thienylmethyl)amine instead of (pyridin-2-ylmethyl)amine. The crude product was purified by crystallization from ethanol (10 mL) to afford the titled compound as the hydrochloride salt as a light-grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20-1.35 (m, 5H), 1.65-1.79 (m, 5H), 1.89 (s, 3H), 2.23 (s, 3H), 4.08 (bs, 1H), 4.71 (d, J=4.57 Hz, 2H), 6.96 (s, 1H), 7.05 (s, 1H), 7.40 (d, J=4.57 Hz, 1H), 7.70 (d, J=6.72 Hz, 1H), 8.07 (s, 1H); MS (ESI) m/z 317.7 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude product was purified by crystallization from ethanol (10 mL)

Sources & evidence

ORD record
ord-0dfe8eb1a5c3423db66af9705e38c50d
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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