Sodium Carbonate → HCID 86633636, compound

HRID 1855519Notes

Reaction equation

HRID 1855519 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.[CH3:13][C:14]1([OH:20])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]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:17]2[CH2:18][CH2:19][C:14]([OH:20])([CH3:13])[CH2:15][CH2:16]2)[N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 156491744-Methylpiperidin-4-ol

Product 1

HCID 86633636HCID 86633636, compoundYield 74.4%

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), 4-methyl-piperidin-4-ol (1.21 g, 8 mmol) and sodium carbonate (1.74 g, 16.0 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 (1.70 g, 72%) as light yellow solid. MS ISP (m/e): 286.1 [(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-48f20ec399af4c50bd787f183d0aac21
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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