Sodium Carbonate → HCID 58336152, compound

HRID 1855456Notes

Reaction equation

HRID 1855456 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 58336152HCID 58336152, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 2,4-dichloropyrimidine-6-carboxylate (1.66 g, 8.0 mmol), pyrrolidine (0.66 mL, 8 mmol) and sodium carbonate (1.54 g, 14.0 mmol) in methanol (8 mL) was stirred for 1 h at 20° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was subsequently washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give crude title compound (0.78 g, 40%) as light yellow solid. MS ISP (m/e): 242.2 [(M+H)+].

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was subsequently washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b21946eef7ef4b15aa5f0970645dc6b4
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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