6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one → 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 279658Notes

Reaction equation

HRID 279658 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19][N:18]=1)[N:9]=[CH:8][N:7](COC(=O)C(C)(C)C)[C:6]2=[O:33]>N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19][N:18]=1)[N:9]=[CH:8][NH:7][C:6]2=[O:33]

Participants

3

Reactant 1

HCID 226250876-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1356711766-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-oneYield 92%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (365 mg, 0.8 mmol) in methanolic ammonia (30 ml of a 3M solution) was stirred at ambient temperature for 16 hours. The volatiles were removed by evaporation, the residue was triturated with ether, the solid was collected by filtration, washed with ether and dried under vacuum to give 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-one (250 mg, 92%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was triturated with ether
  3. filtrationthe solid was collected by filtration
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-458ce6b5cc05497a97933bafa5d664af
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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