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Water → 3-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]-1-methylthieno[3,4-d]pyrimidine-2,4-dione

HRID 1762830
Notes
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Reaction equation

HRID 1762830 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:21](=[O:22])[C:20]4=[CH:23][S:24][CH:25]=[C:19]4[NH:18][C:17]3=[O:26])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:21](=[O:22])[C:20]4=[CH:23][S:24][CH:25]=[C:19]4[N:18]([CH3:31])[C:17]3=[O:26])[CH2:10][CH2:9]2)=[O:7])=[CH:27][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 145003983-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 145004023-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]-1-methylthieno[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

The title compound was prepared by dissolving the 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione from Example 10 (1.8 g, 4.6 mmol) in 10 ml of dimethylformamide at 0° C. After treating this solution with NaH (203 mg, 5 mmol) followed by 720 mg (5 mmol) of methyl iodide, the mixture was stirred at room temperature for 24 hours. The reaction was poured into water and extracted with CH2Cl2. The combined extracts were washed with water and brine and dried over MgSO4. Solvent removal produced a crude product which was purified by flash silica gel chromatography using 2% MeOH/CH2Cl2. The title compound was crystallized from CH2Cl2 /hexane to give a white solid (1.04 g, 54% yield), mp 176°-178° C.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. customSolvent removal
  5. customproduced a crude product which

Sources & evidence

ORD record
ord-493b6785d3d04d8ea6a84bf03b0b9e4f
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04835157

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes