Isopropanol → HCID 11742401, compound

HRID 348031Notes

Reaction equation

HRID 348031 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:25])[CH:3]=1.[H-].[Na+].[CH:28]([OH:31])([CH3:30])[CH3:29]>C1COCC1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[N:8][N:7]3[C:2]([O:31][CH:28]([CH3:30])[CH3:29])=[CH:3][C:4]([CH3:25])=[N:5][C:6]=23)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 210837217-Chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 11742401HCID 11742401, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine (I-3A-4b; 59 mg, 0.15 mmol) in THF (0.5 ml) and isopropanol (0.5 ml) was added NaH (60% dispersion in oil, 30 mg, 0.76 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 0–35% ethyl acetate in hexanes as eluant to afford 8A-1 (59 mg, 95%) as a colorless solid: +ESI MS (M+1) 412.4; 1H NMR (400 MHz, CD2Cl2) δ 7.50–7.36 (m, 6H), 7.23 (d, J=8.7 Hz, 2H), 6.19 (s, 1H), 4.99 (septuplet, J=6.1 Hz, 1H), 2.62 (s, 3H), 1.57 (d, J=5.8 Hz, 6H).

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 8A-1 (59 mg, 95%) as a colorless solid

Sources & evidence

ORD record
ord-6f1ec0114e294c219c69c7d0880f31f6
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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