Hydrochloric Acid → 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid

HRID 1719964Notes

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:25])[CH2:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:26]([O:28]C)=[O:27].[I-].[Li+].Cl>N1C=CC=CC=1.O>[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:25])[CH2:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:26]([OH:28])=[O:27]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (5.72 g) and anhydrous lithium iodide (14.3 g) in dry pyridine (59 ml) was stirred at 120° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure to give a crystalline residue, which was suspended in water (100 ml). The suspension was adjusted to pH 1.7 with conc. hydrochloric acid to yield yellow crystals, which were separated by filtration, washed with water and dried. Recrystallization from N,N-dimethylformamide gave crystalline 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (4.4 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give a crystalline residue, which
customto yield yellow crystals, which
customwere separated by filtration
washwashed with water
customdried
customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record: ord-9b32f028b03c4b05ac6c41566de384fc
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04543356

Reaction notes

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