Cyclopropanecarbonyl chloride → HCID 178429156, compound

HRID 591234Notes

Reaction equation

HRID 591234 reaction equation
[NH2:1][C:2]1[N:7]([NH2:8])[C:6](=[O:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[CH:11]1([C:14](Cl)=O)[CH2:13][CH2:12]1>O1CCOCC1.CN(C)C=O>[CH:11]1([C:14]2[N:1]=[C:2]3[N:3]=[C:4]([CH3:10])[CH:5]=[C:6]([OH:9])[N:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 9131753-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 178429156HCID 178429156, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Intermediate 1 (0.5 g, 3.57 mmol) in a mixture of 1,4-dioxane (4 mL) and N,N-dimethylformamide (1 mL), cyclopropanecarbonyl chloride (ALDRICH, 0.49 mL, 5.35 mmol) was added and the resulting mixture was heated under reflux overnight. The reaction was then concentrated under vacuum yielding a pale yellow solid which was purified by flash chromatography (Si, eluting with DCM:MeOH mixtures, gradient from 100:0% to 90:10%) to yield a beige solid which was re-purified by flash chromatography (Si, eluting with DCM:MeOH mixtures from 100:0 to 85:15%). The title compound was obtained as a white solid.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux overnight
  4. concentrationThe reaction was then concentrated under vacuum
  5. customyielding a pale yellow solid which
  6. customwas purified by flash chromatography (Si, eluting with DCM:MeOH mixtures, gradient from 100:0% to 90:10%)
  7. customto yield a beige solid which
  8. customwas re-purified by flash chromatography (Si, eluting with DCM:MeOH mixtures from 100:0 to 85:15%)

Sources & evidence

ORD record
ord-40d22c08f45947ff8cae76d78e12cea5
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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