Sodium hydride → HCID 10480339, compound

HRID 348032Notes

Reaction equation

HRID 348032 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:11]1[N:16]2[N:17]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[C:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:34])[CH:12]=1.[H-].[Na+]>C1COCC1>[C:1]([N:5]1[CH2:8][CH:7]([O:9][C:11]2[N:16]3[N:17]=[C:18]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:19]([C:20]4[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=4)=[C:15]3[N:14]=[C:13]([CH3:34])[CH:12]=2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2879861-tert-Butyl-3-hydroxyazetidineHCID 210837217-Chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 10480339HCID 10480339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butylazetidin-3-ol (24 mg, 0.19 mmol) and 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine (I-3A-4b; 36 mg, 0.093 mmol) in THF (1 ml) was added NaH (60% dispersion in oil, 9.3 mg, 0.23 mmol). After stirring for 1 hour, the reaction was quenched with water, 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 0–5% methanol in methylene chloride as eluant to afford 9A-1 (26 mg, 59%) as a colorless solid: +ESI MS (M+1) 481.4; 1H NMR (400 MHz, CD2Cl2) δ 7.50–7.36 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.99 (s, 1H), 5.10–5.02 (m, 1H), 3.76–3.70 (br m, 2H), 3.49–3.43 (br m, 2H), 2.60 (s, 3H), 1.00 (s, 9H).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted from saturated aqueous NaHCO3 with ethyl acetate
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified on a Biotage™ Flash 12M column
  6. customto afford 9A-1 (26 mg, 59%) as a colorless solid

Sources & evidence

ORD record
ord-3d57872e9c0c454e81ef0e1a6cfc960c
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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