Sodium hydride → HCID 86618412, compound

HRID 2098717Notes

Reaction equation

HRID 2098717 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([CH3:9])(=[O:8])=[O:7].[H-].[Na+].Br[CH2:13][C:14]1[S:22][C:21]2[C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[N:19][C:18]([Cl:29])=[N:17][C:16]=2[CH:15]=1>O1CCCC1>[Cl:29][C:18]1[N:19]=[C:20]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[C:21]2[S:22][C:14]([CH2:13][N:5]([CH2:4][CH2:3][O:2][CH3:1])[S:6]([CH3:9])(=[O:8])=[O:7])=[CH:15][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3522477N-(2-methoxyethyl)methanesulfonamideHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618412HCID 86618412, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-Methoxy-ethyl)-methanesulfonamide (61 mg) in tetrahydrofuran (1.5 ml) under nitrogen was added sodium hydride, 60% dipersion in mineral oil, (18 mg). The reaction mixture was stirred at room temperature for 30 minutes. 6-Bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (140 mg) was added. The reaction mixture was stirred at room temperature for 2 hours and then 50° C. for 5 hours. The solvents were removed in vacuo to give a crude product. This was purified by flash chromatography to give N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(2-methoxy-ethyl)-methanesulfonamide (124 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. wait50° C. for 5 hours
  3. customThe solvents were removed in vacuo
  4. customto give a crude product
  5. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-21cf1d8d27c4414aa3d1dec03bd5bfd3
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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