2-Chloropyrimidine → HCID 59579963, compound

HRID 2279625Notes

Reaction equation

HRID 2279625 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][NH:10][N:9]=1.Cl[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1>O1CCOCC1>[NH2:7][C:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:9]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 23665647Potassium tert-butoxideHCID 178469928HCID 178469928, compound

Product 1

HCID 59579963HCID 59579963, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Potassium tert-butoxide (2.4 g, 21.23 mmol) is added to a mixture of ethyl 3-amino-1H-pyrazole-4-carboxylate (3.0 g, 19.3 mmol) and 2-chloropyrimidine (2.2 g, 19.3 mmol) in 50 mL of anhydrous dioxane. The reaction mixture is heated to 100° C. and stirred for 2 h. The solvent is removed in vacuo, and the residue is partitioned between EtOAc and water (50 mL each). The aqueous layer is extracted two more times with EtOAc (40 mL each), and the combined organic extracts are dried (Na2SO4), filtered, and evaporated in vacuo to give a yellow/brown oily solid. This crude product is triturated with EtOAc to give the title compound as a white solid.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between EtOAc and water (50 mL each)
  3. extractionThe aqueous layer is extracted two more times with EtOAc (40 mL each)
  4. dry with materialthe combined organic extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a yellow/brown oily solid
  8. customThis crude product is triturated with EtOAc

Sources & evidence

ORD record
ord-475efe149fc94e2995f9169a8c05b27f
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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