Formic Acid → 6-(2-Fluorophenyl)-5-(4-methoxyphenyl)-4-[(3R)-piperidin-3-yloxy]furo[2,3-d]pyrimidine

HRID 2189078Notes

Reaction equation

HRID 2189078 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][C:15]2[C:16]3[C:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[F:38])[O:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:9]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:22]1[O:21][C:17]2[N:18]=[CH:19][N:20]=[C:15]([O:14][C@@H:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[C:16]=2[C:23]=1[C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 284Formic Acid2×HCID 671602904-{[(3R)-1-Benzylpiperidin-3-yl]oxy}-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

Product 1

HCID 671600016-(2-Fluorophenyl)-5-(4-methoxyphenyl)-4-[(3R)-piperidin-3-yloxy]furo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Add 300 mg of palladium black to an argon-blanketed solution of 2600 mg (4.69 mmol) of 4-{[(3R)-1-benzylpiperidin-3-yl]oxy}-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]-pyrimidine in 25 ml of a 4.4% solution of formic acid in methanol and stir at room temperature for five hours. Then add another 300 mg of palladium black and 0.9 ml of formic acid and stir at room temperature for a further 16 hours. After filtering off the catalyst, wash the catalyst residue with methanol/water. Concentrate the filtrate under reduced pressure, stir the residue in acetonitrile, filter off and dry under reduced pressure. 1376 mg (68% of theory) of the desired product are obtained.

Workup

  1. stirringstir at room temperature for a further 16 hours
  2. filtrationAfter filtering off the catalyst
  3. washwash the catalyst residue with methanol/water
  4. concentrationConcentrate the filtrate under reduced pressure
  5. stirringstir the residue in acetonitrile
  6. filtrationfilter off
  7. customdry under reduced pressure

Sources & evidence

ORD record
ord-ba6d8c2ab72f4976ae35b74253984fba
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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