Potassium Carbonate → HCID 66900224, compound

HRID 1631388Notes

Reaction equation

HRID 1631388 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[N:14]=2)[CH:7]=1.Cl[CH2:29][CH:30]1[CH2:34][O:33][C:32]([CH3:36])([CH3:35])[O:31]1.C(=O)([O-])[O-].[K+].[K+].[Br-].[Na+]>CN(C=O)C>[CH3:35][C:32]1([CH3:36])[O:31][CH:30]([CH2:29][O:27][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=2[C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[N:14]=2)[CH2:34][O:33]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 253881Sodium BromideHCID 86664578(R)-ethyl 5-(2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 66900224HCID 66900224, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-ethyl 5-(2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (Example 86, Step C, 140 mg, 0.378 mmol), 4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (114 mg, 0.756 mmol), potassium carbonate (261 mg, 1.89 mmol) and sodium bromide (77.8 mg, 0.756 mmol) in dry DMF (5 mL) was heated at 100° C. for 14 days. The mixture was concentrated and the residue purified by chromatography to afford the title compound (45 mg, 25% yield). MS (apci) m/z=485.0 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-bc972725f1044d95bb2c8a8e505e5833
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

Loading…