Acetyl chloride → 1-Acetyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione

HRID 1762828Notes

Reaction equation

HRID 1762828 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.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C(Cl)Cl>[C:29]([N:18]1[C:19]2=[CH:25][S:24][CH:23]=[C:20]2[C:21](=[O:22])[N:16]([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:28][CH:27]=3)[CH2:9][CH2:10]2)[C:17]1=[O:26])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 145003983-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 145003991-Acetyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by suspending the 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione (2.0 g, 5 mmol) of Example 10 in CH2Cl2 and treating it with acetyl chloride (469 mg, 6 mmol) and triethylamine (1 equivalent). After stirring at room temperature for 24 hours, the organic phase was washed with water and brine and dried over MgSO4. Solvent removal produced a crude product which was purified by flash silica gel chromatography using EtOAc/hexane (1/1). The title compound was crystallized from CH2Cl2 /hexane to give a white solid (337 mg, 15% yield), mp 150°-151° C.

Workup

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customSolvent removal
  4. customproduced a crude product which

Sources & evidence

ORD record
ord-5938cb94956946dc9ab7ebc3fe3d5737
Source dataset
uspto-grants-1989_05
Patent number
US04835157

Reaction notes

Loading…