tert-Butyl acetate → HCID 86670279, compound

HRID 472839Notes

Reaction equation

HRID 472839 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21].C(O[C:29]([CH3:32])([CH3:31])[CH3:30])(=O)C.Cl(O)(=O)(=O)=O>C(Cl)Cl>[C:29]([O:24][CH:19]([C:3]1[C:4]([CH3:18])=[N:5][C:6]2[N:7]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=2)[C:2]=1[Cl:1])[C:20]([O:22][CH3:23])=[O:21])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 86670273Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

Product 1

HCID 86670279HCID 86670279, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (3550 mg, 9.69 mmol) in tert-butyl acetate (50 mL, 9.69 mmol) at room temperature was added CH2Cl2 (30 mL) followed by perchloric acid (1.250 mL, 14.54 mmol). The reaction mixture was stirred for 5 h at room temperature. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic phase was washed with saturated NaHCO3 and dried over sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (2.7 mg, 66%). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.07-8.00 (m, 1H), 7.89 (dt, J=6.7, 1.9 Hz, 1H), 7.48-7.37 (m, 2H), 6.93 (s, 1H), 5.68 (s, 1H), 3.75 (s, 3H), 2.69 (s, 3H), 1.29 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-afd8e2129b2e4aa3ad637de62179ea0d
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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