Potassium Carbonate → HCID 66900695, compound

HRID 1631357Notes

Reaction equation

HRID 1631357 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]3[N:15]=2)[CH:5]=[C:6]([OH:8])[CH:7]=1.Br[CH2:29][CH2:30][O:31][CH3:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]3[N:15]=2)[CH:5]=[C:6]([O:8][CH2:29][CH2:30][O:31][CH3:32])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 86664575HCID 86664575, compound

Product 1

HCID 66900695HCID 66900695, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-ethyl 5-(2-(3-fluoro-5-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (Example 76 Step B, 174 mg, 0.470 mmol), 1-bromo-2-methoxyethane (196 mg, 1.41 mmol), and K2CO3 (325 mg, 2.35 mmol) were suspended in DMF (5 mL) and stirred at ambient temperature for 15 hours. The crude reaction mixture was purified by reverse phase HPLC (0-60% acetonitrile/water) to provide yield the title compound (183 mg, 91% yield). MS (apci) m/z=429.0 (M+H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by reverse phase HPLC (0-60% acetonitrile/water)
  3. customto provide

Sources & evidence

ORD record
ord-88a60ef1d57f43758cd21fe1db88248a
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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