Dimethylformamide → HCID 58313859, compound

HRID 624807Notes

Reaction equation

HRID 624807 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:18][CH2:17]3)[N:12]3[N:19]=[CH:20][CH:21]=[C:11]3[N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:22].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN([CH:33]=[O:34])C>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:18][CH2:17]3)[N:12]3[N:19]=[CH:20][C:21]([CH:33]=[O:34])=[C:11]3[N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:22]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 58314012HCID 58314012, compound

Product 1

HCID 58313859HCID 58313859, compoundYield 65%

Conditions

Temperature
45 °C

Procedure

To 2-chloro-4-(7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)phenol (582 mg, 1.84 mmol) in DMF (4.5 mL) cooled to 0° C. was added phosphorous oxychloride (0.514 mL, 5.52 mmol) dropwise. The reaction mixture was stirred while warming to 45° C. over 3 h. This was cooled down to 0° C. and added slowly to an ice-cold solution of 2M NaOH while stirring. Upon completion, the mixture was stirred at room temperature for 1 h. The resulting solid was filtered off and washed with water to provide 412 mg (65%) of 5-(3-chloro-4-hydroxyphenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. LCMS (ES): >95% pure, m/z 344 [M+1]+.

Workup

  1. temperatureThis was cooled down to 0° C.
  2. stirringwhile stirring
  3. stirringUpon completion, the mixture was stirred at room temperature for 1 h
  4. filtrationThe resulting solid was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-da91864dc85a4fb78784d84781b10611
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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