Tetrahydrofuran → HCID 66693624, compound

HRID 472821Notes

Reaction equation

HRID 472821 reaction equation
[CH3:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:5]2[N:19]=[CH:20][CH:21]=[C:4]2[N:3]=1.CC(C[AlH]CC(C)C)C.C1COCC1>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:5]2[N:19]=[CH:20][CH:21]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 66693755HCID 66693755, compound

Product 1

HCID 66693624HCID 66693624, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 5-methyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carboxylate (950 mg, 3.38 mmol) in CH2Cl2 (50 mL) was added DIBAL-H, 1M in THF (16.9 mL, 16.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 h before being quenched with saturated NH4Cl solution. The aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (482 mg, 56.3%). 1H-NMR (500 MHz, CDCl3) δ ppm 1.64 (1H, t, J=4.9 Hz), 2.45 (3H, s), 2.78 (3H, s), 4.58 (2H, d, J=4.9 Hz), 6.60 (1H, d, J=2.4 Hz), 7.34-7.40 (2H, m), 7.42-7.49 (2H, m), 8.00 (1H, d, J=2.4 Hz).

Workup

  1. custombefore being quenched with saturated NH4Cl solution
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-752c6b6143dc437ba54a9d0c97c42a0d
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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