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 657726Notes

Reaction equation

HRID 657726 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 yield 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-e2b56753051f47a792cc01f2be86531b
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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