Ethanol → HCID 87523410, compound

HRID 1855429Notes

Reaction equation

HRID 1855429 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](C)([O-:16])C.[K+].[CH2:19](O)C>>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH2:12][CH3:19])=[O:10])[CH:5]=[C:6]([O:16][CH2:14][CH3:13])[N:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 87523410HCID 87523410, compoundYield 43%

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 2,4-dichloropyrimidine-6-carboxylate (2.07 g, 10.0 mmol) and potassium tert.-butoxide (1.12 g, 10.0 mmol) in ethanol (50 mL) was stirred for 4 h at 60° C. The mixture was cooled to, insoluble material was removed by filtration, and the filtrate was evaporated under reduced pressure. The oily residue was partitioned between ethyl acetate and brine, and the organic layer was dried over sodium sulfate and evaporated under reduced pressure to give crude title compound (0.98 g, 43%) as colorless oil. MS ISP (m/e): 231.1 [(M+H)+].

Workup

  1. temperatureThe mixture was cooled to, insoluble material
  2. customwas removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe oily residue was partitioned between ethyl acetate and brine
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c4c948dc9d3c4a4bae00eba53911165e
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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