Dimethylformamide → HCID 57752942, compound

HRID 225995Notes

Reaction equation

HRID 225995 reaction equation
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[C:12]([CH3:13])=[C:11]([Cl:14])[N:10]2[N:15]=[CH:16][CH:17]=[C:9]2[N:8]=1.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[Cl:6][C:7]1[C:12]([CH3:13])=[C:11]([Cl:14])[N:10]2[N:15]=[CH:16][C:17]([CH:22]=[O:23])=[C:9]2[N:8]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 123660735,7-Dichloro-6-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 57752942HCID 57752942, compound

Conditions

Temperature
70 °C

Procedure

To N,N-dimethyl formamide (9 mL) under nitrogen at room temperature was added POCl3 (3mL) and the resulting slurry was stirred for 5 min. 5,7-Dichloro-6-methylpyrazolo[1,5-a]pyrimidine (5 g) was slowly added and resulting thick mixture was heated at 70° C. for 3 h. The mixture was poured onto ice and basified with sodium hydroxide (5 g). The residue was filtered and the dried precipitate chromatographed on silica gel (eluting with CH2Cl2→20% ethyl acetate/CH2Cl2) to give the title compound (3.74 g); mp 137-139° C.

Workup

  1. customresulting thick mixture
  2. additionThe mixture was poured onto ice
  3. filtrationThe residue was filtered
  4. customthe dried precipitate chromatographed on silica gel (eluting with CH2Cl2→20% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-4f1ced06e97842ca88ff4459d989516e
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

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