Sodium hydride → HCID 86618404, compound

HRID 2098688Notes

Reaction equation

HRID 2098688 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][NH:5][S:6]([CH3:9])(=[O:8])=[O:7].[H-].[Na+].Br[CH2:14][C:15]1[S:23][C:22]2[C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:20][C:19]([Cl:30])=[N:18][C:17]=2[CH:16]=1>O1CCCC1>[Cl:30][C:19]1[N:20]=[C:21]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[C:22]2[S:23][C:15]([CH2:14][N:5]([CH2:4][CH2:3][N:2]([CH3:10])[CH3:1])[S:6]([CH3:9])(=[O:8])=[O:7])=[CH:16][C:17]=2[N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 425315HCID 425315, compoundHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618404HCID 86618404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2-dimethylamino-ethyl)-methanesulfonamide (50 mg) in tetrahydrofuran under nitrogen was added sodium hydride, 60% dispersion in mineral oil, (13 mg). The reaction mixture was stirred at room temperature for 30 minutes, the 6-Bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine in tetrahydrofuran (5 ml) was added dropwise. The reaction mixture was stirred for 5 days. The solvents were removed in vacuo to give a crude product which was purified by flash chromatography to yield N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(2-dimethylamino-ethyl)-methanesulfonamide (35 mg).

Workup

  1. stirringThe reaction mixture was stirred for 5 days
  2. customThe solvents were removed in vacuo
  3. customto give a crude product which
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-968f6c926f804d779078b33c5692b46b
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…