Water → HCID 86648994, compound

HRID 2188664Notes

Reaction equation

HRID 2188664 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[N:12]=[C:11]([N:13]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH3:14])[CH:10]=[N:9][CH:8]=1.O.CN([CH:23]=[O:24])C>>[Cl:6][C:7]1[C:8]([CH:23]=[O:24])=[N:9][CH:10]=[C:11]([N:13]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH3:14])[N:12]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 61360573HCID 61360573, compound

Product 1

HCID 86648994HCID 86648994, compoundYield 71%

Procedure

Phosphoryl chloride (0.43 mL) was added dropwise to DMF (1 mL) at 0° C. The mixture was stirred for 15 min, and a solution of 6-chloro-N-(cyclopropylmethyl)-N-methylpyrazin-2-amine (0.46 g) in DMF (1 mL) was added dropwise thereto. The mixture was stirred at 50° C. for 16 hr, water (5 mL) was added at 0° C., and the mixture was stirred at room temperature for 1.5 hr. The mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane) to give the title compound (0.37 g, 71%) as a pale-yellow oil.

Workup

  1. stirringThe mixture was stirred at 50° C. for 16 hr
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. extractionThe mixture was extracted with ethyl acetate
  4. extractionThe aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ff717fe9f1e4823bef73cbdb334f677
Source dataset
uspto-grants-2012_12
Patent number
US08324201B2

Reaction notes

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