Phosphorus oxychloride → Methyl 2-amino-4-chloroquinazoline-7-carboxylate

HRID 449337Notes

Reaction equation

HRID 449337 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[CH:5][C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:19])=O>>[NH2:1][C:2]1[N:11]=[C:10]([Cl:19])[C:9]2[C:4](=[CH:5][C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136346397Methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Product 1

HCID 59496646Methyl 2-amino-4-chloroquinazoline-7-carboxylateYield 92.3%

Procedure

A solution of methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate (500 mg, 2.28 mmol) and phosphoryl chloride (4 mL, 42.9 mmol) was stirred at 110° C. for 6 h. The starting material was consumed and the reaction mixture was concentrated to give the crude product (500 mg, 92.2%) as an oil. 1H NMR (300 MHz, DMSO) δ 3.9 (s, 3H), 7.79 (dd, 1H), 8.05 (d, 1H), 8.13 (d, 1H); Analytic LCMS (M+H)+: m/z=238.0.

Workup

  1. customThe starting material was consumed
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1e9676d3372f4425b5fa3701bb112f1b
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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