Dimethylformamide → HCID 178490015, compound

HRID 411595Notes

Reaction equation

HRID 411595 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=4)=[N:16][C:17](=[O:18])[C:12]3=[C:11]([CH:28]([CH3:30])[CH3:29])[NH:10]2)=[C:4]([Cl:31])[CH:3]=1.C([Mg]Cl)(C)C.CN([CH:40]=[O:41])C>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([CH:40]=[O:41])[CH:3]=[C:4]([Cl:31])[C:5]=1[N:9]1[C:13]2=[N:14][C:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)=[N:16][C:17](=[O:18])[C:12]2=[C:11]([CH:28]([CH3:30])[CH3:29])[NH:10]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 178418918HCID 178418918, compoundHCID 178490011HCID 178490011, compound

Product 1

HCID 178490015HCID 178490015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A two-neck flask was flame-dried, charged with 1-(4-bromo-2,6-dichlorophenyl)-3-isopropyl-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one (250 mg, 0.48 mmol) and 4 mL of THF, and placed under an argon atmosphere. The solution was cooled to 0° C. and isopropylmagnesium chloride (0.26 mL, 0.523 mmol) was added dropwise via syringe. The reaction was stirred at −78° C. for 2 min and DMF (0.08 mL, 1.06 mmol) was added via syringe. The reaction was stirred at −78° C. for 15 min and at RT for 30 min. The reaction was quenched with 10% aq. citric acid and extracted with EtOAc. The organic extract was washed with water then brine, dried (MgSO4), and evaporated. Purification by column chromatography on silica gel using 2:1 hexanes-EtOAc as eluent afforded 68 mg (30%) of the title as a white solid, mp 212-214° C. Mass Spec: 469(M−H)−.

Workup

  1. customA two-neck flask was flame-dried
  2. stirringThe reaction was stirred at −78° C. for 15 min and at RT for 30 min
  3. customThe reaction was quenched with 10% aq. citric acid
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialbrine, dried (MgSO4)
  8. customevaporated
  9. customPurification by column chromatography on silica gel using 2:1 hexanes-EtOAc as eluent
  10. customafforded 68 mg (30%) of the title as a white solid, mp 212-214° C

Sources & evidence

ORD record
ord-0738c8057d1c460aad602c41f5ae8c75
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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