Methanol → tert-Butyl 6-methyl-4-oxo-4,5,6,8-tetrahydropyrido[3,4-d]pyrimidine-7(1H)-carboxylate

HRID 453153Notes

Reaction equation

HRID 453153 reaction equation
[CH3:1][CH:2]1[N:12](C(C2C=CC=CC=2)C)[CH2:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[CH2:3]1.[CH:21]([O-:23])=[O:22].[NH4+].[CH3:25]O.[CH2:27]1[CH2:31]OC[CH2:28]1>[Pd]>[C:27]([O:22][C:21]([N:12]1[CH:2]([CH3:1])[CH2:3][C:4]2[C:9](=[O:10])[NH:8][CH:7]=[N:6][C:5]=2[CH2:11]1)=[O:23])([CH3:28])([CH3:31])[CH3:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 1361587816-methyl-7-(1-phenyl-ethyl)-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 136158782tert-Butyl 6-methyl-4-oxo-4,5,6,8-tetrahydropyrido[3,4-d]pyrimidine-7(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 6-methyl-7-(1-phenyl-ethyl)-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one, (6.8 g, 25.2 mmol), ammonium formate (7.96 g, 126 mmol), BOC-anhydride (8.27 g, 37.9 mmol), MeOH (250 mL), and THF (167 mL) is added 10% Pd/C (1.36 g, 20% w/w) and the reaction is heated at reflux for 3 h. The mixture is then filtered through a Celite® pad and the filterate is concentrated. The residue is purified via FCC (1-10% MeOH/DCM) to give the title compound. MS (ESI) m/z 266.1 (M+H).

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux for 3 h
  3. filtrationThe mixture is then filtered through a Celite® pad
  4. concentrationthe filterate is concentrated
  5. customThe residue is purified via FCC (1-10% MeOH/DCM)

Sources & evidence

ORD record
ord-48ea23f88d6143658fe300f2ece4b7fe
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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