1-Butanol → HCID 86664565, compound

HRID 1631302Notes

Reaction equation

HRID 1631302 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[N:3]=1.Cl.Cl.[F:18][C:19]1[CH:20]=[C:21]([C@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[C:22]([O:25][CH3:26])=[N:23][CH:24]=1.C(N(C(C)C)CC)(C)C.C(O)CCC>CCOC(C)=O>[F:18][C:19]1[CH:20]=[C:21]([C@H:27]2[CH2:31][CH2:30][CH2:29][N:28]2[C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]3[N:3]=2)[C:22]([O:25][CH3:26])=[N:23][CH:24]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 58063474Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylateHCID 66847679(R)-5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine dihydrochloride

Product 1

HCID 86664565HCID 86664565, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (Preparation B, 0.75 g, 3.32 mmol), (R)-5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine dihydrochloride (0.984 g, 3.66 mmol), diisopropylethylamine (2.32 mL, 13.3 mmol) and n-butanol (1.11 mL) were heated at 90° C. for 48 hours. The reaction mixture was diluted with EtOAc and the mixture was washed with water, brine and saturated NaHCO3. The organic layer was dried with MgSO4, filtered and concentrated afford a dark orange oil. The oil was purified by silica chromatography, eluting with a 50-80% EtOAc/Hexane gradient, to afford (R)-ethyl 5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.72 g, 56.2%) as a yellow foam. MS (apci) m/z=386.0 (M+H).

Workup

  1. washthe mixture was washed with water, brine and saturated NaHCO3
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customafford a dark orange oil
  6. customThe oil was purified by silica chromatography
  7. washeluting with a 50-80% EtOAc/Hexane gradient

Sources & evidence

ORD record
ord-17847951198f46e493b30f28472380b7
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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