Sulfuric Acid → HCID 9976371, compound

HRID 859979Notes

Reaction equation

HRID 859979 reaction equation
S(=O)(=O)(O)O.[CH:6]1([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:19]([CH:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)O)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)[CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[H][H]>C(O)C.[Pd]>[CH2:27]([C:19]1[C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10]3)[N:17]=2)=[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]2[N:20]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10407742HCID 10407742, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9976371HCID 9976371, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of concentrated sulfuric acid (9 mL, 169 mmol) in ethanol (25 mL) was added 10% palladium on carbon (200 mg) and a solution of {3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (350 mg, 0.908 mmol) in ethanol (5 mL). The reaction mixture was stirred under 55 PSI of hydrogen for 3 days. The reaction mixture was filtered through a pad of celite. Saturated aqueous sodium bicarbonate solution was added to the filtrate until basic. The resulting mixture was concentrated on rotovap to remove the excess ethanol, then extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (29:1 dichloromethane:methanol) provided 4-(2-benzylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopentyl-2-pyrimidinamine (221 mg, 66%) as an off-white solid. 1H NMR (CDCl3) δ 8.45 (d, 1H), 8.25 (d, 1H), 8.19 (d, 1H), 7.30–7.13 (m, 6H), 6.82 (m, 1H), 6.63 (d, 1H), 5.12 (d, 1H), 4.52 (s, 2H), 4.35 (m, 1H), 2.03 (m, 2H), 1.78–1.50 (m, 6H); MS m/z 370 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. additionSaturated aqueous sodium bicarbonate solution was added to the filtrate until basic
  3. concentrationThe resulting mixture was concentrated on rotovap
  4. customto remove the excess ethanol
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-b4725b74b22040f0aabf6ca61631b463
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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