Potassium Carbonate → HCID 59279465, compound

HRID 1098115Notes

Reaction equation

HRID 1098115 reaction equation
[OH:1][C@H:2]([CH2:7][O:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH3:6])=[O:4].Cl[C:13]1[N:18]=[CH:17][N:16]=[C:15]2[N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:20]=[CH:21][C:14]=12.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:19]1[C:15]2=[N:16][CH:17]=[N:18][C:13]([O:1][C@H:2]([CH2:7][O:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH3:6])=[O:4])=[C:14]2[CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112655704-Chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-D]pyrimidineHCID 59279538HCID 59279538, compound

Product 1

HCID 59279465HCID 59279465, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

(R)-methyl 2-hydroxy-3-isopropoxypropanoate D1a (500 mg, 3.08 mmol), 4-chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine B1 (817 mg, 3.08 mmol) and potassium carbonate (0.186 mL, 3.08 mmol) were suspended in acetonitrile (15 mL). The reaction was heated to 130° C. for 4 hours in the microwave reactor and cooled to ambient temperature. The reaction mixture was evaporated to dryness and the resulting residue was dissolved in EtOAc (25 mL), and washed sequentially with saturated NH4Cl (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. Purification by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane afforded (2R)-methyl 2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-isopropoxypropanoate D1b (965 mg).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe resulting residue was dissolved in EtOAc (25 mL)
  4. washwashed sequentially with saturated NH4Cl (50 mL) and saturated brine (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customPurification
  10. washby flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane

Sources & evidence

ORD record
ord-8c11680a4f5a46f693cf32967f543d3c
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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