1-(Bromomethyl)-3-methanesulfonylbenzene → HCID 57933143, compound

HRID 1432184Notes

Reaction equation

HRID 1432184 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[CH:3]=1.Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=1>>[CH3:29][S:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][N:14]1[CH2:13][CH2:12][CH:11]([NH:10][C:9]2[C:4]3[CH:3]=[C:2]([Cl:1])[S:17][C:5]=3[N:6]=[CH:7][N:8]=2)[CH2:16][CH2:15]1)(=[O:27])=[O:28]

Participants

3

Reactant 2

HCID 224566941-(Bromomethyl)-3-methanesulfonylbenzeneHCID 579331476-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 57933143HCID 57933143, compound

Procedure

The title compound was prepared (70 mg, 43%) from 6-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine (100 mg, 0.37 mmol) and 1-(bromomethyl)-3-(methylsulfonyl)benzene (139 mg, 0.55 mmol) by following the general procedure described for Preparation 12. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 7.95 (s, 1H), 7.80 (d, 1H), 7.60 (d, 1H), 7.50 (t, 1H), 7.05 (s, 1H), 5.25 (d, 1H), 4.20 (m, 1H), 3.60 (s, 2H), 3.05 (s, 3H), 2.80 (m, 2H), 2.20 (m, 2H), 2.05 (m, 2H), 1.60 (m, 2H). MS (EST) m/z: Calculated: 436.98; Observed: 437.2 (M++1).

Workup

  1. customdescribed for Preparation 12

Sources & evidence

ORD record
ord-7fecb9a3b6024729839e97c54faa185e
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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