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

HRID 2189077Notes

Reaction equation

HRID 2189077 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.[CH:39]([OH:41])=[O:40]>CO.[Pd]>[CH:39]([OH:41])=[O:40].[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 AcidHCID 671602904-{[(3R)-1-Benzylpiperidin-3-yl]oxy}-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

Product 1

HCID 671612866-(2-Fluorophenyl)-5-(4-methoxyphenyl)-4-[(3R)-piperidin-3-yloxy]furo[2,3-d]pyrimidine formate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 400 mg of palladium black to an argon-blanketed solution of 510 mg (1.00 mmol) of 4-{[(3R)-1-benzylpiperidin-3-yl]oxy}-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine in 5 ml of a 4.4% solution of formic acid in methanol, and stir at room temperature for two days. After filtering off the catalyst, wash the catalyst residue with methanol/water. Concentrate the filtrate under reduced pressure and purify the residue by means of preparative RP-HPLC (eluent: water/acetonitrile gradient with 0.1% formic acid). 70 mg (12% of theory, 80% purity) of the desired product are obtained.

Workup

  1. filtrationAfter filtering off the catalyst
  2. washwash the catalyst residue with methanol/water
  3. concentrationConcentrate the filtrate under reduced pressure
  4. custompurify the residue by means of preparative RP-HPLC (eluent: water/acetonitrile gradient with 0.1% formic acid)

Sources & evidence

ORD record
ord-73d103a924ce47379c5caaacb2baeede
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…