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Acetic Anhydride → HCID 13911281, compound

HRID 247476
Notes
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Reaction equation

HRID 247476 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:22](=[O:23])[C:21]3[S:24][CH:25]=[CH:26][C:20]=3[NH:19][C:18]2=[O:27])[CH2:11][CH2:10]1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([N:19]1[C:20]2[CH:26]=[CH:25][S:24][C:21]=2[C:22](=[O:23])[N:17]([CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]2)[C:18]1=[O:27])(=[O:30])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 139112783-[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 13911281HCID 13911281, compoundYield 57%

Procedure

A solution of 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]thieno[3,2-d]pyrimidine-2,4-dione (2.6 g, 6.73 mmol) in acetic anhydride (30 ml) was heated to reflux for 5 hours. Acetic anhydride was removed in vacuo. The residue was dissolved in toluene, and the toluene was removed in vacuo. This process was repeated twice to remove any residual acetic anhydride. The residue was purified by flash chromatography on silica gel 60 (60 g) using 2.5% methanol in methylene chloride as eluant to give the product (1.65 g, 57% yield) as an off-white solid, mp 156°-158° C.

Workup

temperature
to reflux for 5 hours
  • customAcetic anhydride was removed in vacuo
  • dissolutionThe residue was dissolved in toluene
  • customthe toluene was removed in vacuo
  • customto remove any residual acetic anhydride
  • customThe residue was purified by flash chromatography on silica gel 60 (60 g)
  • Sources & evidence

    ORD record
    ord-0fe08c0d2017454b8d1c1f6cfb0c5f09
    Source dataset
    uspto-grants-1987_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04707550

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes