Sodium Methoxide → THIENO[2,3-D]PYRIMIDINE, 4-MORPHOLINYL-

HRID 2098697Notes

Reaction equation

HRID 2098697 reaction equation
N1C2C(=C([C:10]3[N:11]=[C:12]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:13]4[S:18][C:17](C=O)=[CH:16][C:14]=4[N:15]=3)C=CC=2)C=C1.C[O-].[Na+]>CO>[N:21]1([C:12]2[C:13]3[S:18][CH:17]=[CH:16][C:14]=3[N:15]=[CH:10][N:11]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86618406HCID 86618406, compound

Product 1

HCID 2809163THIENO[2,3-D]PYRIMIDINE, 4-MORPHOLINYL-Yield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-(1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (54 mg) in anhydrous methanol (8 ml) was added phosphorus sulphone (34 mg), followed by sodium methoxide (148u1). The reaction mixture was stirred at room temperature for 4.5 hours, then evaporated onto silica and purified by flash chromatography to give 2-(1H-indol-4-yl)-6-((E)-2-methanesulfonyl-vinyl))-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (30 mg).

Workup

  1. customevaporated onto silica
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-61a3a30b6ab047399399be39b9c7d98d
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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