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Potassium Carbonate → 4-(2-Butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine

HRID 423164
Notes
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Reaction equation

HRID 423164 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](F)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].Cl.[CH3:15][C:16]1([CH3:21])[CH2:20][CH2:19][NH:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:18]2[CH2:19][CH2:20][C:16]([CH3:21])([CH3:15])[CH2:17]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 467360573,3-Dimethylpyrrolidine--hydrogen chloride (1/1)HCID 596619664-(2-Butynyloxy)-5,6-difluoropyrimidine

Product 1

HCID 115072224-(2-Butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
70 °C

Procedure

0.36 g of 4-(2-butynyloxy)-5,6-difluoropyrimidine, 0.25 g of 3,3-dimethylpyrrolidine hydrochloride and 0.62 g of potassium carbonate are added to 1 ml of acetonitrile, then the reaction mixture is stirred at 70° C. for 5 hours. Then saturated aqueous solution of ammonium chloride is added to the reaction mixture which is cooled to about room temperature, and extract with t-butyl methyl ether three times. The organic layers are joined, dried with anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidine-1-yl)pyrimidine (referred as the present compound (8) hereinafter).

Workup

  1. temperatureis cooled to about room temperature
  2. extractionextract with t-butyl methyl ether three times
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8456e423dfda4991a67bb009dd26559a
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101753B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes