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-methylpyrimidinyl)amino)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 1421050Notes

Reaction equation

HRID 1421050 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]1C=C(C)N=[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[N:18]=[CH:19][CH:5]=[C:10]([CH3:11])[N:9]=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 1357447356-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidinyl)amino)ethoxy)-3,4-dihydroquinazolin-4-oneYield 183.1%

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-methylpyrimidinyl)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-24b99ac54d214b8aadee2b5423c51edb
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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