4-chloro-5,6-dimethylthieno[2,3-d]pyrimidine → HCID 11530562, compound

HRID 1432181Notes

Reaction equation

HRID 1432181 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.Cl.[CH:15]1([CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:15]1([CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([NH:28][C:2]3[C:3]4[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:24][CH2:23]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 2902124-chloro-5,6-dimethylthieno[2,3-d]pyrimidineHCID 532558864-Piperidinamine, 1-(cyclohexylmethyl)-, hydrochloride (1:2)

Product 1

HCID 11530562HCID 11530562, compound

Procedure

The title compound was prepared (81 mg, 28%) from 4-chloro-5,6-dimethylthieno[2,3-d]pyrimidine (325 mg, 1.21 mmol) and 1-(cyclohexylmethyl)piperidin-4-amine dihydrochloride (160 mg, 0.81 mmol) by following the general procedure described for Preparation 6. 1H NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 5.36 (d, 1H), 4.22 (m, 1H), 2.80 (d, 2H), 2.44 (s, 3H), 2.41 (s, 3H), 2.21-2.09 (m, 7H), 1.79-1.45 (m, 6H), 1.20 (m, 4H), 0.88 (m, 2H); MS (ESI) m/z: Calculated for C20H31N4S, 359.23; Observed: 359.2 (M++1).

Workup

  1. customdescribed for Preparation 6

Sources & evidence

ORD record
ord-b1bc316497eb4c5e98b5a963673258d9
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

Loading…