Ethyl orthoformate → 6-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1485539Notes

Reaction equation

HRID 1485539 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH2:12](OC(OCC)OCC)C>CCCCCC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:12][NH:11][C:9](=[O:10])[C:3]=2[N:4]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 107497043-Amino-6-chloropyridine-2-carboxamide

Product 1

HCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-oneYield 94.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A suspension of 3-amino-6-chloropicolinamide (2.56 g, 14.9 mmol) in triethylorthoformate (45 mL, 271 mmol) was refluxed for 6 h. The reaction mixture was cooled to room temperature, diluted with hexane, and then filtered. The filter cake was washed with hexane and dried under vacuum to give 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one (2.55 g, 94%) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian 400 MHz) δ 7.88 (1H, d, J=8.4 Hz), 8.14 (1H, d, J=8.4 Hz), 8.20 (1H, s), 12.65 (1H, brs). m/z=182.06 [M+1]+.

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationfiltered
  3. washThe filter cake was washed with hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-808904afe01941a98831ff93e13cc7ec
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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