Water → HCID 13060509, compound

HRID 354902Notes

Reaction equation

HRID 354902 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.CO[CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24].O>CN(C)C=O>[C:13]([NH:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:1][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1)(=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 90770Dimethyl methoxymethylenemalonateHCID 13060453HCID 13060453, compound

Product 1

HCID 13060509HCID 13060509, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-7-pivalamidoquinazoline (10.5 g) and dimethyl methoxymethylenepropanedioate (10.9 g) in N,N-dimethylformamide (32 ml) was stirred at 100° C. for 1 hour and 25 minutes. After the reaction mixture was cooled to ambient temperature, water was added. The resulting solid was separated by filtration, washed with water and dried. The crystals were recrystallized from a mixture of ethyl acetate and ethanol to give crystalline dimethyl [[7-pivalamido-4-quinazolinylamino]methylene]propanedioate (13.7 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to ambient temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water
  4. customdried
  5. customThe crystals were recrystallized from a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-bd0cd3ddb1cb430982a2dbe3927c7703
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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