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

HRID 1045997Notes

Reaction equation

HRID 1045997 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>>[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

3

Reactant 2

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

Product 1

HCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Conditions

Temperature
145 °C

Procedure

3-amino-6-chloro-pyridine-2-carboxylic acid amide (7.45 g, 43.41 mmol) is taken up in triethylorthoformate (150 mL) and stirred for 3 h at 145° C. After cooling the precipitate formed is filtered off, washed with Et2O, dried and 6-chloro-3H-pyrido[3,2-d]pyrimidin-4-one (HPLC-MS: tRet=0 min; MS (M+H)+=182) is obtained.

Workup

  1. temperatureAfter cooling the precipitate
  2. customformed
  3. filtrationis filtered off
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-81a5e221ad984bde9318edb7564dd633
Source dataset
uspto-grants-2013_10
Patent number
US08569316B2

Reaction notes

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