Ammonia → 6-[[(4-Acetylphenyl)-2-propynylamino]methyl]-4(3H)-quinazolinone

HRID 1722697Notes

Reaction equation

HRID 1722697 reaction equation
CC(C)(C)C(OC[N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][CH:24]=3)[CH2:20][C:21]#[CH:22])[CH:14]=2)[N:9]=[CH:8]1)=O.N>CO>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([N:19]([CH2:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][NH:7][C:16]3=[O:17])[CH2:20][C:21]#[CH:22])=[CH:28][CH:27]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 146499992,2-Dimethylpropanoic acid, [6-[[(4-acetylphenyl)-2-propynylamino]methyl]-4-oxo-3(4H)-quinazolinyl]methyl ester

Product 1

HCID 1358557606-[[(4-Acetylphenyl)-2-propynylamino]methyl]-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.34 g (5.25 mmol) of 2,2-dimethylpropanoic acid, [6-[[(4-acetylphenyl)-2-propynylamino]methyl]-4-oxo-3(4H)-quinazolinyl]methyl ester (Example 1) is added a solution of 500 ml of methanol saturated with ammonia at 20° C. The solution is stirred at room temperature for eighteen hours. The solution is concentrated to give a solid which is recrystallized from ethanol to give the product as a pink solid; mp 197°-199° C.

Workup

  1. concentrationThe solution is concentrated
  2. customto give a solid which
  3. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-40d77011147340bebf53d74779b27c33
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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