Triethylamine → 1-(2,6-Dichloro-5-fluoro-4-pyrimidinyl)-3-methyl-3-pyrrolidinol

HRID 1366521Notes

Reaction equation

HRID 1366521 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([F:9])=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH3:18][C:19]1([OH:24])[CH2:23][CH2:22][NH:21][CH2:20]1>C1COCC1.CO>[Cl:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:22][CH2:23][C:19]([CH3:18])([OH:24])[CH2:20]2)[C:5]([F:9])=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 133889932,4,6-Trichloro-5-fluoropyrimidineHCID 145784583-Methylpyrrolidin-3-ol

Product 1

HCID 866369741-(2,6-Dichloro-5-fluoro-4-pyrimidinyl)-3-methyl-3-pyrrolidinolYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,4,6-trichloro-5-fluoropyrimidine (0.476 g, 2.36 mmol) and triethylamine (0.36 mL, 2.60 mmol) in THF was added 3-methyl-3-pyrrolidinol (0.239 g, 2.36 mmol) in THF and MeOH (2 mL). The reaction was stirred at room temperature for 2.5 hours, and then the solvent was removed in vacuo. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organics were dried (Na2SO4) and evaporated to provide 1-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-3-methyl-3-pyrrolidinol as an orange solid (0.486 g, 77%). LCMS: (M+H)+=266.1.

Workup

  1. customthe solvent was removed in vacuo
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7351a1117ce24f539e5a4271bdaea714
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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