Sodium hydride → 3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2262128Notes

Reaction equation

HRID 2262128 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:21][C:22]1[S:30][C:29]2[C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:27][C:26]([Cl:37])=[N:25][C:24]=2[CH:23]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:21][C:22]2[S:30][C:29]3[C:28]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[N:27][C:26]([Cl:37])=[N:25][C:24]=3[CH:23]=2)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholineHCID 67189774tert-Butyl 3-methanesulfonamidopyrrolidine-1-carboxylate

Product 1

HCID 866184073-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-Methanesulfonylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.47 g) in DMF (5 mL) was added NaH (63 mg). The mixture was stirred for 40 min. then a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (0.52 g) in DMF (5 mL) was added via cannular. The resulting mixture was stirred at R.T. for 5 h. An aqueous work-up followed by purification on silica gave 3-[(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (384 mg).

Workup

  1. stirringThe resulting mixture was stirred at R.T. for 5 h
  2. customAn aqueous work-up followed by purification on silica

Sources & evidence

ORD record
ord-94f15ed053ac4274a1e93c879d07adee
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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