Dimethylformamide → HCID 57752942, compound

HRID 1446052Notes

Reaction equation

HRID 1446052 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

A suspension prepared by adding POCl3 (3 mL) to N,N-dimethylformamide (9 mL) under nitrogen flow at room temperature was stirred for 5 min. To the suspension was slowly added 5,7-dichloro-6-methylpyrazolo[1,5-a]pyrimidine (5 g) and the reaction was carried out by heating the resulting viscous mixture solution at 70° C. for 3 hrs. The reaction mixture was poured into ice and the resultant solution was made alkaline with sodium hydroxide (5 g). The precipitate was filtered off and the dried precipitate was purified by silica gel chromatography (eluting with CH2Cl2→20% ethyl acetate/CH2Cl2) to obtain the title compound (3.74 g); the melting point was between 137 and 139° C.

Workup

  1. customA suspension prepared
  2. additionThe reaction mixture was poured into ice
  3. filtrationThe precipitate was filtered off
  4. customthe dried precipitate was purified by silica gel chromatography (eluting with CH2Cl2→20% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-e715dd89c9b043088e83719fef50dcb9
Source dataset
uspto-grants-2010_02
Patent number
US07667036B2

Reaction notes

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