Tributylamine → Methyl 6-(2-chloro-6-fluorophenyl)-5,7-dihydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1866093Notes

Reaction equation

HRID 1866093 reaction equation
CO[C:3](=[O:17])[CH:4]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:5]([O:7]C)=O.[NH2:18][C:19]1[NH:23][N:22]=[CH:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25].C(N(CCCC)CCCC)CCC>CO>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[C:4]1[C:3]([OH:17])=[N:18][C:19]2[N:23]([N:22]=[CH:21][C:20]=2[C:24]([O:26][CH3:27])=[O:25])[C:5]=1[OH:7]

Participants

5

Reactant 3

HCID 7622TributylamineHCID 272904methyl 3-aminopyrazole-4-carboxylateHCID 2784495HCID 2784495, compound

Product 1

HCID 178498902Methyl 6-(2-chloro-6-fluorophenyl)-5,7-dihydroxypyrazolo[1,5-a]pyrimidine-3-carboxylateYield 139.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, 15 g (57.5 mmol) of dimethyl(2-chloro-6-fluorophenyl)malonate were mixed with 9.4 g (57.5 mmol) of methyl 5-amino-1H-pyrazole-4-carboxylate and 15 ml (63.3 mmol) of tri-n-butylamine. The mixture was then stirred at 185° C. for 8 hours, during which time methanol was distilled off. After cooling, excess tri-n-butylamine was carefully decanted off. Concentration under reduced pressure gave 27 g of methyl 6-(2-chloro-6-fluorophenyl)-5,7-dihydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (logPs=0.55; content according to HPLC: 83%).

Workup

  1. distillationwas distilled off
  2. temperatureAfter cooling
  3. customexcess tri-n-butylamine was carefully decanted off
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-b5b3338ebd164be9941fb56cff60bd2e
Source dataset
uspto-grants-2009_12
Patent number
US07629294B2

Reaction notes

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