Sodium Carbonate → HCID 11544891, compound

HRID 2217991Notes

Reaction equation

HRID 2217991 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18](O)[CH:17]=[C:16]([CH3:21])[N:15]=2)=[N:6]1.C(=O)([O-])[O-].[Na+].[Na+].P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:18]1[CH:17]=[C:16]([CH3:21])[N:15]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])[N:6]=2)[N:19]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178429300HCID 178429300, compound

Product 1

HCID 11544891HCID 11544891, compound

Conditions

Temperature
100 °C

Procedure

300 mg (0.90 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-4-pyrimidinol (example I, step 6) are suspended in 2 ml of phosphoryl chloride and stirred at 100° C. After the reaction is complete, a concentrated aqueous sodium carbonate solution is added, and the mixture is extracted with diethyl ether. The organic phase is dried over magnesium sulfate and filtered, and the solvent is removed in vacuo. 256 mg (77% of theory) of the product are obtained.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. custom256 mg (77% of theory) of the product are obtained

Sources & evidence

ORD record
ord-eb30c41f0a5c41cab4aeed9265200784
Source dataset
uspto-grants-2008_08
Patent number
US07410973B2

Reaction notes

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