Water → Ethyl 1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 662014Notes

Reaction equation

HRID 662014 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH2:13][CH3:14])[N:5]=[C:4]2[N:15]([CH2:18][CH3:19])[N:16]=[CH:17][C:3]=12.C(N(C(C)C)CC)(C)C.[O:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1.O>CN1CCCC1>[CH2:18]([N:15]1[C:4]2=[N:5][C:6]([CH2:13][CH3:14])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]([NH:35][CH:32]3[CH2:33][CH2:34][O:29][CH2:30][CH2:31]3)=[C:3]2[CH:17]=[N:16]1)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 59683218Ethyl 4-chloro-1,6-diethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 59683211Ethyl 1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylateYield 111.3%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

To a solution of ethyl 4-chloro-1,6-diethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (380 g) in 1-methylpyrrolidine (3166 mL) was added diisopropylethylamine (469.8 mL) and tetrahydro-2H-pyran-4-ylamine (163 g) and the mixture was heated at reflux for 16 h. The cooled mixture was treated with water (12 liters) and extracted with ethyl acetate (6×1250 mL). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness to afford 520 g of a dark brown oil. The product was purified by flash chomatography on silica using ethyl acetate/cyclohexane @1:4-1:2 as eluant to afford 336 g of the title compound. LC-MS m/z 347 (M+H)+, 3.02 min (ret time).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with ethyl acetate (6×1250 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-bb3c0e4bfc4c43db99f49780a69942bd
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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