Acetic Acid → HCID 178428313, compound

HRID 1040125Notes

Reaction equation

HRID 1040125 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:17]=[C:18]([C:23]3[S:27][C:26]([C:28]([OH:34])([CH3:33])[C:29]([F:32])([F:31])[F:30])=[N:25][CH:24]=3)[CH:19]=[C:20]([CH3:22])[CH:21]=2)[N:10]=1)C1C=CC=CC=1.C(O)C.C(O)(=O)C.[H][H]>[Pd].CO.C(OCC)(=O)C>[CH3:22][C:20]1[CH:21]=[C:16]([NH:15][C:11]2[N:10]=[C:9]([OH:8])[CH:14]=[CH:13][N:12]=2)[CH:17]=[C:18]([C:23]2[S:27][C:26]([C:28]([OH:34])([CH3:33])[C:29]([F:32])([F:30])[F:31])=[N:25][CH:24]=2)[CH:19]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 67430329HCID 67430329, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 178428313HCID 178428313, compoundYield 78.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10 wt %) (50 mg, 0.05 mmol) was added to a flask that was evacuated and backfilled with argon (3×). A solution of 2-[5-(3-{[4-(benzyloxy)pyrimidin-2-yl]-amino}-5-methylphenyl)-1,3-thiazol-2-yl]-1,1,1-trifluoropropan-2-ol (Example 94B-1, 230 mg, 0.47 mmol) in a mixture of methanol (4 mL), ethanol (3 mL) and ethyl acetate (2 mL) was added followed by the addition of acetic acid (50 μL, 0.87 mmol). A hydrogen balloon was placed on top of the reaction and the reaction was evacuated/backfilled with hydrogen (5×). The reaction was stirred overnight at room temperature. The mixture was then filtered through celite, washing with methanol. The filtrate was concentrated under reduced pressure and purified by Chromatography on silica gel (30-100% ethyl acetate in hexanes) to provide 145 mg (0.367 mmol, 77%) of 2-({3-methyl-5-[2-(1,1,1-trifluoro-2-hydroxypropan-2-yl)-1,3-thiazol-5-yl]phenyl}amino)pyrimidin-4-ol as a white solid.

Workup

  1. customwas evacuated
  2. additionwas added
  3. filtrationThe mixture was then filtered through celite
  4. washwashing with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by Chromatography on silica gel (30-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-411d3f81774a497d97a28b33ac7ad22b
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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