4-Chloro-6-isopropylthieno(2,3-d)pyrimidine → N-(1-(3,5-difluorobenzyl)piperidin-4-yl)-6-isopropylthieno[2,3-d]pyrimidin-4-amine

HRID 1432160Notes

Reaction equation

HRID 1432160 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:26]=[C:27]([F:29])[CH:28]=1)[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1>>[F:14][C:15]1[CH:16]=[C:17]([CH:26]=[C:27]([F:29])[CH:28]=1)[CH2:18][N:19]1[CH2:20][CH2:21][CH:22]([NH:25][C:2]2[C:3]3[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 27576274-Chloro-6-isopropylthieno(2,3-d)pyrimidineHCID 221824001-[(3,5-Difluorophenyl)methyl]piperidin-4-amine

Product 1

HCID 11524197N-(1-(3,5-difluorobenzyl)piperidin-4-yl)-6-isopropylthieno[2,3-d]pyrimidin-4-amine

Procedure

The title compound was prepared (264 mg, 56%) from 4-chloro-6-isopropylthieno[2,3-d]pyrimidine (0.25 g, 1.18 mmol) and 1-(3,5-difluorobenzyl)piperidin-4-amine (0.4 g, 1.77 mmol) by following the general procedure described for Preparation 6. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 6.90 (m, 2H), 6.80 (s, 1H), 6.70 (m, 1H), 4.95 (d, 1H), 4.20 (m, 1H), 3.50 (s, 2H), 3.20 (m, 1H), 2.85 (m, 2H), 2.25 (m, 2H), 2.10 (m, 2H), 1.60 (m, 2H), 1.40 (d, 6H). MS (ESI) m/z: Calculated: 402.5; Observed: 403.1 (M++1).

Workup

  1. customdescribed for Preparation 6

Sources & evidence

ORD record
ord-ef6572712cad487f9b138af6877271c9
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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