Potassium Iodide → 4-Amino-8-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]pyrido[2,3-d]pyrimidin-5(8H)-one

HRID 1499713Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Br:21][C:22]1[C:23]([CH3:34])=[C:24]([Cl:33])[CH:25]=[C:26]([CH:30](Cl)[CH3:31])[C:27]=1[O:28][CH3:29]>CN(C)C=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][N:8]([CH:30]([C:26]3[CH:25]=[C:24]([Cl:33])[C:23]([CH3:34])=[C:22]([Br:21])[C:27]=3[O:28][CH3:29])[CH3:31])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one (0.80 g, 4.9 mmol), cesium carbonate (2.4 g, 7.3 mmol) and potassium iodide (82 mg, 0.49 mmol) in N,N-dimethylformamide (20 mL) was added 3-bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzene (1.47 g, 4.93 mmol) and the mixture was stirred at 140° C. for 1 hour. The mixture was diluted with water and ethyl acetate. The precipitate was collected and dried to give the desired compound. LCMS calculated for C17H17BrClN4O2 (M+H)+: m/z=423.0; Found: 423.0.

Workup

customThe precipitate was collected
customdried

Sources & evidence

ORD record: ord-982214d31d01418e9ced8fb219f70fae
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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