2-(Bromomethyl)benzonitrile → HCID 11524108, compound

HRID 1432165Notes

Reaction equation

HRID 1432165 reaction equation
[Cl:1][C:2]1[S:17][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:4]=2[C:3]=1[CH3:18].Br[CH2:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>>[Cl:1][C:2]1[S:17][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:12][CH2:13][N:14]([CH2:20][C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]#[N:24])[CH2:15][CH2:16]3)[C:4]=2[C:3]=1[CH3:18]

Participants

3

Reactant 2

HCID 895992-(Bromomethyl)benzonitrileHCID 22182425HCID 22182425, compound

Product 1

HCID 11524108HCID 11524108, compound

Procedure

The title compound was prepared (100 mg, 75%) from 6-chloro-5-methyl-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine (95 mg, 0.336 mmol) and 2-(bromomethyl) benzonitrile (73 mg, 0.37 mmol) by following the general procedure described for Preparation 12. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 7.65 (d, 1H), 7.55 (m, 2H), 7.35 (m, 1H), 5.30 (d, 1H), 4.25 (m, 1H), 3.7 (s, 2H), 2.85 (m, 2H), 2.50 (s, 3H), 2.40 (m, 2H), 2.10 (m, 2H), 1.40 (m, 2H). MS (ESI) m/z: Calculated: 397.92; Observed: 398.2 (M++1).

Workup

  1. customdescribed for Preparation 12

Sources & evidence

ORD record
ord-1dd29a72cdd44e14a2c9342cfefb461b
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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