Ammonium formate → HCID 58782236, compound

HRID 1268701Notes

Reaction equation

HRID 1268701 reaction equation
[C:1]1([C:7]2[C:11](/[CH:12]=[CH:13]/[C@@H:14]([OH:24])[CH2:15][C@@H:16]([OH:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:9]([C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:32]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C@@H:14]([OH:24])[CH2:15][C@@H:16]([OH:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:10]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:9]([C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:32]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 21075628HCID 21075628, compound

Product 1

HCID 58782236HCID 58782236, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A flask containing (3R,5S,E)-ethyl 7-(3,5-diphenyl-1-(2-(phenylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)-3,5-dihydroxyhept-6-enoate, 28 (0.227 g), ammonium formate (0.500 g) and palladium on carbon (0.050 g) in ethanol (10 mL) is heated to 80° C. for 2 h adding extra portions of catalyst and ammonium formate every 45 min. The reaction mixture is left at ambient temperature for 16 h, then filtered through celite and concentrated. The resulting residue is partitioned between ethyl acetate and water and the organic layer dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography affords (3R,5R)-ethyl 7-(3,5-diphenyl-1-(2-(phenylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)-3,5-dihydroxyheptanoate, 31 (0.162 g) and (4R,6R)-6-(2-(3,5-diphenyl-1-(2-(phenylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)ethyl)-4-hydroxy-tetrahydropyran-2-one, 32 (0.023 g).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated
  3. customThe resulting residue is partitioned between ethyl acetate and water
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-05475098e25c4e64b5f5cac3cf50c392
Source dataset
uspto-grants-2007_04
Patent number
US07199126B2

Reaction notes

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