Ammonium formate → 4-(Morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 8716

Reaction equation

HRID 8716 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[N:18]1([C:14]2[C:15]3[CH2:16][CH2:17][NH:8][CH2:9][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219836347-Benzyl-4-(morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 219836204-(Morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Benzyl-4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 5a (0.55 g, 1.77 mmol) was dissolved in methanol (35 mL) under nitrogen. 10% Pd/C (0.55 g) was added under nitrogen followed by ammonium formate (1.12 g, 17.72 mmol) and the mixture was heated to reflux for 12 h. The catalyst was removed by filtration, washed with MeOH and the filtrate was concentrated. Flash column chromatography eluting with 5% MeOH/CH2Cl2 containing 0.5% of NH4OH gave 0.27 g of 4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 6a as a pale yellow dense liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 h
  3. customThe catalyst was removed by filtration
  4. washwashed with MeOH
  5. concentrationthe filtrate was concentrated
  6. washFlash column chromatography eluting with 5% MeOH/CH2Cl2 containing 0.5% of NH4OH

Sources & evidence

ORD record
ord-4369f92349b7406ebd1712953537ed2e
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Linked notes

Loading…