Ethyl chloroformate → Ethyl 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxothieno[3,2-d]pyrimidine-1-carboxylate

HRID 247477Notes

Reaction equation

HRID 247477 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.[H-].[Na+].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][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[N:19]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:18]2=[O:27])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 139112783-[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 13911283Ethyl 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxothieno[3,2-d]pyrimidine-1-carboxylateYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]thieno[3,2-d]pyrimidine-2,4-dione (2.62 g, 6.77 mmol) and sodium hydride (60% in mineral oil, prewashed with pentane, 325 mg, 8.13 mmol) in N,N-dimethylformamide (50 ml) was allowed to equilibrate for one hour. Ethyl chloroformate (0.78 ml, 8.13 mmol) was added to the resultant solution, and stirred at room temperature for 16 hours. The solution was poured into ice water (200 ml) and the resultant solid was collected by filtration, washed with water and air dried. The solid was purified by flash chromatography on silica gel 60 (100 g) using 1% methanol in methylene chloride as eluant to give the product (0.88 g, 28% yield) as a colorless solid, mp 121°-122° C.

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. washwashed with water and air
  3. customdried
  4. customThe solid was purified by flash chromatography on silica gel 60 (100 g)

Sources & evidence

ORD record
ord-454b3365cdd74e3b928faedcfcc4bdbe
Source dataset
uspto-grants-1987_11
Patent number
US04707550

Reaction notes

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