Lithium iodide → 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid

HRID 1719962Notes

Reaction equation

[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:22]([O:24]C)=[O:23].[I-].[Li+]>N1C=CC=CC=1>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:22]([OH:24])=[O:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (5.42 g) and anhydrous lithium iodide (13.55 g) in dry pyridine (54 ml) was stirred at 100° C. for 1.5 hours. The reaction mixture was cooled to give crystals which were collected by filtration and washed with pyridine. The crystals were suspended in water (200 ml). The suspension was adjusted to pH 2.5-3.0 with conc. hydrochloric acid to give yellow crystals, which were separated by filtration, washed with water and dried. The crude crystals were washed with a mixture of chloroform and methanol (1:1) two times and dried. There was obtained crystalline 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (3.80 g).

Workup

temperatureThe reaction mixture was cooled
customto give crystals which
filtrationwere collected by filtration
washwashed with pyridine
customto give yellow crystals, which
customwere separated by filtration
washwashed with water
customdried
washThe crude crystals were washed with a mixture of chloroform and methanol (1:1) two times
customdried

Sources & evidence

ORD record: ord-ba2d8f206a8c4a0b9e203d8104757f0c
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04543356

Reaction notes

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