Potassium Iodide → 2-Isopropyl-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid 4-pyridin-3-yl-butyl ester

HRID 1583395Notes

Reaction equation

[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]1[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][N:8]1[C:7]2=[O:21])[CH3:3].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31]Cl)[CH:23]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OC(=O)C)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][O:19][C:18]([C:16]2[CH:15]=[CH:14][C:9]3[N:8]([CH:17]=2)[C:7](=[O:21])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)[N:10]=3)=[O:20])[CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 0.70 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, 0.50 g of 4-(3-pyridinyl)butylchloride, 0.40 g of potassium iodide and 0.39 g of potassium carbonate in 12 ml of dimethylformamide was stirred over night at a bath temperature of 50° C. The reaction mixture was diluted with ethylacetate, washed with water, dried (potassium carbonate) and concentrated. The residue was chromatographed on 75 g of silica gel eluting with ethyl acetate to give 0.46 g of a yellow solid which was recrystallized from ethyl acetate-hexane to give 0.33 g (32%), mp 95°-96° C.

Workup

washwashed with water
dry with materialdried (potassium carbonate)
concentrationconcentrated
customThe residue was chromatographed on 75 g of silica gel eluting with ethyl acetate

Sources & evidence

ORD record: ord-e442beb8ab094892863502f88436e092
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551460

Reaction notes

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