Dimethylformamide → HCID 86646773, compound

HRID 913280Notes

Reaction equation

HRID 913280 reaction equation
CN(C)C=O.P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[N:17]=[C:16]([C:18](=[NH:22])[NH:19][C:20]#[N:21])[CH:15]=[CH:14][N:13]=1.[CH2:23](Cl)[Cl:24]>C(#N)C>[Cl:24][C:23]1[N:22]=[C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[N:17]=2)[N:19]=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178512299HCID 178512299, compound2×

Product 1

HCID 86646773HCID 86646773, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice-cooled solution of N,N-dimethylformamide (8.5 mL, 110 mmol) in methylene chloride (100 mL) was added phosphorus oxychloride (8.0 mL, 87 mmol) dropwise, and the mixture was stirred for 0.5 h. The resulting mixture was poured into a cold (0° C.) suspension of 2-chloro-N-cyano-4-pyrimidinecarboximidamide (i.e., the product of Step A) (13 g, 73 mmol) in acetonitrile (200 mL). The resulting mixture was stirred overnight in an ice bath. The mixture was passed through a short silica gel pad, eluted with 30% ethyl acetate in hexanes, and concentrated under reduced pressure to give 7 g of the title compound as a white solid.

Workup

  1. stirringThe resulting mixture was stirred overnight in an ice bath
  2. washeluted with 30% ethyl acetate in hexanes
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2756d7f1cc684dfc8ad3a127d1c7d536
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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