6-Benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine → 4-methoxy-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine

HRID 241843Notes

Reaction equation

HRID 241843 reaction equation
C([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[CH:13][N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[CH3:17][O:16][C:15]1[C:10]2[CH2:9][NH:8][CH2:19][CH2:18][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 1

HCID 581035816-Benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 509892144-methoxy-5H,6H,7H,8H-pyrido[4,3-d]pyrimidineYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

250 mL flask was charged with 6-benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (4.08 g, 16.0 mmol), 10% palladium on charcoal (400 mg) and methanol (100 mL). The reaction was evacuated and purged with hydrogen three times, and hydrogenated (1 atm) overnight. The mixture was filtered through a “Dry disk” membrane filter, and concentrated in vacuo to give an orange oil (2.56 g).

Workup

  1. customThe reaction was evacuated
  2. custompurged with hydrogen three times, and hydrogenated (1 atm) overnight
  3. filtrationThe mixture was filtered through a “
  4. customDry disk” membrane
  5. filtrationfilter
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6053f009d46445ff8a5091eb527fff94
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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