Sodium Bicarbonate → HCID 66897311, compound

HRID 1409263Notes

Reaction equation

HRID 1409263 reaction equation
[CH3:1][C:2]1[CH:17]=[C:5]2[N:6]=[C:7]([NH2:16])[CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:4]2[N:3]=1.Cl[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:34])([CH3:33])[CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=1)=[O:20].C([O-])(O)=O.[Na+]>N1C=CC=CC=1.ClCCl>[CH3:34][C:27]([C:24]1[CH:23]=[CH:22][C:21]([C:19](=[O:20])[NH:16][C:7]2[CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:4]3[N:3]=[C:2]([CH3:1])[CH:17]=[C:5]3[N:6]=2)=[CH:26][CH:25]=1)([CH3:33])[CH2:28][C:29]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amineHCID 86652281HCID 86652281, compound

Product 1

HCID 66897311HCID 66897311, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a 50 ml pear flask was added 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 200 mg, 0.89 mmol) in pyridine (5 ml) to give a light yellow solution. A solution of methyl 3-(4-(chlorocarbonyl)phenyl)-3-methylbutanoate (230 mg, 0.89 mmol) in dichloromethane (1 ml) was added to the reaction mixture at room temperature, which was then stirred for 72 h. Saturated NaHCO3 was added and pyridine was mostly removed in vacuo. The residue was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous layer was extracted one more time with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, 30-40% ethyl acetate/hexanes) to give the titled product (60 mg, 15% yield) as a yellow foam. 1H NMR (CHLOROFORM-d) δ: 8.61 (s, 2H), 8.10-8.15 (m, 8H), 7.87-7.92 (m, 5H), 7.54-7.59 (m, 8H), 7.50-7.54 (m, 5H), 6.28 (s, 2H), 3.54 (s, 8H), 2.68-2.71 (m, 5H), 2.50 (s, 8H), 1.49 (s, 6H); ESI-MS: m/z 443.3 (M+H)+.

Workup

  1. customto give a light yellow solution
  2. custompyridine was mostly removed in vacuo
  3. customThe residue was partitioned between saturated NaHCO3 and ethyl acetate
  4. extractionthe aqueous layer was extracted one more time with ethyl acetate
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (SiO2, 30-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-81339e9e34ca4ba49d6775051a9c49dd
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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