Sodium hydride → HCID 86618403, compound

HRID 2098686Notes

Reaction equation

HRID 2098686 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:17][C:18]1[S:26][C:25]2[C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[N:23][C:22]([Cl:33])=[N:21][C:20]=2[CH:19]=1>O1CCCC1>[Cl:33][C:22]1[N:23]=[C:24]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[C:25]2[S:26][C:18]([CH2:17][N:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[S:10]([CH3:13])(=[O:12])=[O:11])=[CH:19][C:20]=2[N:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1237764HCID 1237764, compoundHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618403HCID 86618403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2-Morpholin-4-yl-ethyl)-methanesulfonamide in tetrahydrofuran under nitrogen was added sodium hydride, 60% dispersion in mineral (16 mg). The mixture was stirred at room temperature for 40 minutes. A solution of 6-Bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (125 mg) in tetrahydrofuran (5 ml) was added. The reaction mixture was stirred at room temperature for 3.5 hours, then 50° C. for 3.5 hours. 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-morpholin-4-yl-ethyl)-methanesulfonamide (138 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3.5 hours
  2. wait50° C. for 3.5 hours
  3. customThe solvents were removed in vacuo
  4. customto give a crude product which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-1c9acc310eb641d29e049cb63bec5726
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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