Potassium Carbonate → (4-Amino-3-cyano-pyrazolo[3,4-d]pyrimidin-1-yl)-acetic acid tert-butyl ester

HRID 1798741Notes

Reaction equation

HRID 1798741 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]#[N:12])[C:3]=12.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:9]=[C:10]([C:11]#[N:12])[C:3]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 178510695HCID 178510695, compound

Product 1

HCID 59242680(4-Amino-3-cyano-pyrazolo[3,4-d]pyrimidin-1-yl)-acetic acid tert-butyl esterYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-amino-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile (76.6 g, 0.476 mol) and potassium carbonate (197 g, 1.427 mmol) in DMF (680 mL) at 0° C. was added tert-butyl chloroacetate (68.1 mL, 0.476 mol) dropwise while maintaining the internal temperature below 20° C. The resulting mixture was stirred for 22 h, filtered and washed with EtOAc (100 mL×2). The solid obtained was suspended in ice water (1.5 L), filtered, washed with ice water (500 mL) and ether (100 mL×2), then dried in vacuo to afford tert-butyl 2-(4-amino-3-cyano-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (81.6 g, 62.3% yield).

Workup

  1. temperaturewhile maintaining the internal temperature below 20° C
  2. filtrationfiltered
  3. washwashed with EtOAc (100 mL×2)
  4. customThe solid obtained
  5. filtrationfiltered
  6. washwashed with ice water (500 mL) and ether (100 mL×2)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a840c85a9f7546ce8cbbe79a58604f37
Source dataset
uspto-grants-2013_01
Patent number
US08343975B2

Reaction notes

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