Ethyl orthoformate → Pyrido[4,3-d]pyrimidin-4(3H)-one, 7-chloro-

HRID 1050348Notes

Reaction equation

HRID 1050348 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]([NH2:11])=[O:10].[CH2:12](OC(OCC)OCC)C>C(OCC)C>[Cl:8][C:6]1[N:5]=[CH:4][C:3]2[C:9](=[O:10])[NH:11][CH:12]=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1185985571279815-28-9

Product 1

HCID 136980669Pyrido[4,3-d]pyrimidin-4(3H)-one, 7-chloro-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

4-Amino-6-chloro-pyridine-3-carboxamide (2, 4.5 g, 26.23 mmol) was added to a pressure tube and triethylorthoformate (30 mL) was added. The reaction vessel was sealed and heated to 140° C. for 11 h. After the cyclization was complete, the reaction mixture was concentrated under reduced pressure, and to the solid obtained was added diethyl ether. The solid was filtered, washed with diethyl ether and dried in vacuum to afford 7-chloro-3H-pyrido[4,3-d]pyrimidin-4-one (3) as brown solid. MS (ESI) m/z 181.90 [M+1]+.

Workup

  1. customThe reaction vessel was sealed
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto the solid obtained
  4. filtrationThe solid was filtered
  5. washwashed with diethyl ether
  6. customdried in vacuum

Sources & evidence

ORD record
ord-07f6b7946eda4e4398127e5ff5b53256
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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