Formic Acid → 5,6,7,8-Tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 241839Notes

Reaction equation

HRID 241839 reaction equation
C([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[CH:13][NH:14][C:15](=[O:16])[C:10]=2[CH2:9]1)C1C=CC=CC=1.C(N(CC)CC)C.C(O)=O>CO.[OH-].[Pd+2].[OH-]>[N:12]1[C:11]2[CH2:17][CH2:18][NH:8][CH2:9][C:10]=2[C:15](=[O:16])[NH:14][CH:13]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 1355929356-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one2×

Product 1

HCID 1356276285,6,7,8-Tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one (Intermediate 1, 18.0 g, 0.0738 mol), triethylamine (48 mL, 0.34 mol), palladium hydroxide (10 g, 0.07 mol) in methanol (242 mL) was heated to 60° C. Formic acid (7.6 mL, 0.20 mol) was added dropwise to the mixture over a 15 minute period. The mixture was heated at 65° C. for three hours, allowed to cool, and filtered over Celite. The filtrate was concentrated under vacuum to yield the title compound as a yellow solid which was used as such for the next step (9.62 g, 77.6%). MS: 152.2 [M+1]+.

Workup

  1. temperatureThe mixture was heated at 65° C. for three hours
  2. temperatureto cool
  3. filtrationfiltered over Celite
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-31beb19418344fafa4e5a9713d4fd74d
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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