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

HRID 2262121Notes

Reaction equation

HRID 2262121 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 (148 ul). 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-a57232e9e42b4aa1bcbf9f98b0e61417
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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