Ethanol → HCID 11246113, compound

HRID 915861Notes

Reaction equation

HRID 915861 reaction equation
Cl[C:2]1[C:3]2[C:4](=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=2)[N:5]=[CH:6][N:7]=1.[CH2:25]([OH:27])[CH3:26].[H-].[Na+]>O1CCCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=[C:3]3[C:2]([O:27][CH2:25][CH3:26])=[N:7][CH:6]=[N:5][C:4]=23)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 58959477HCID 58959477, compound

Product 1

HCID 11246113HCID 11246113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine (I-2A-1c; 50 mg, 0.133 mmol) and ethanol (0.016 ml, 0.27 mmol) in tetrahydrofuran (1.5 ml) was added NaH (60% dispersion in oil, 14 mg, 0.33 mmol). After stirring for 1 hour, the reaction was extracted from saturated aqueous NaHCO3 with ethyl acetate, the combined organic layers were dried (MgSO4), concentrated and purified on a Biotage® Flash 12M column using a solvent gradient of 0-20% ethyl acetate in hexanes as eluant to afford 12A-1 (46 mg, 92%) as a colorless solid: +ESI MS (M+1) 385.4; 1H NMR (400 MHz, CD2Cl2) δ 8.56 (s, 1H), 7.58-7.46 (m, 6H), 7.34 (d, J=8.7 Hz, 2H), 4.70 (q, J=7.1 Hz, 2H), 1.53 (t, J=7.1 Hz, 3H).

Workup

  1. extractionthe reaction was extracted from saturated aqueous NaHCO3 with ethyl acetate
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified on a Biotage® Flash 12M column
  5. customto afford 12A-1 (46 mg, 92%) as a colorless solid

Sources & evidence

ORD record
ord-fdc7ff24c99f40e082f9ca8771067351
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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