Ammonium formate → HCID 58782236, compound

HRID 350766Notes

Reaction equation

HRID 350766 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
86 °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 86° 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-45a5b3cc213442df853a842496d85a1b
Source dataset
uspto-grants-2007_02
Patent number
US07183285B2

Reaction notes

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