Cyclopropanecarbonyl chloride → HCID 16070221, compound

HRID 1710707Notes

Reaction equation

HRID 1710707 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[N:17]=[C:16]([NH2:18])[CH:15]=[N:14][C:13]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[N:20]=1>N1C=CC=CC=1>[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[N:17]=[C:16]([NH:18][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[CH:15]=[N:14][C:13]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[N:20]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 16071661HCID 16071661, compound

Product 1

HCID 16070221HCID 16070221, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropanecarbonyl chloride (0.028 mL, 0.30 mmol) was added to a stirred solution of 6-(2-furyl)-5-(2-methylpyrimidin-4-yl)pyrazin-2-amine (Example 9, 38 mg, 0.15 mmol) in pyridine (0.5 mL). The mixture was heated to 80° C. in a sealed tube and stirred for 3 h. The crude reaction was concentrated to dryness and the residue was diluted with ethyl acetate and washed with aqueous sodium bicarbonate 4%. The organic layer was dried (Na2SO4) and evaporated. The residue was purified with flash silica gel chromatography (30% ethyl acetate in hexanes). Concentration in vacuo of the product-rich fractions provided the titled compound as a pale-yellow solid (12 mg, 25%).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated to dryness
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous sodium bicarbonate 4%
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified with flash silica gel chromatography (30% ethyl acetate in hexanes)
  8. concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record
ord-8b486725ba7540588476d178ac252cf0
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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