Water → HCID 86665993, compound

HRID 2258428Notes

Reaction equation

HRID 2258428 reaction equation
[Si:1]([NH:8][C:9]1[N:10]=[C:11]([Cl:18])[C:12]2[CH:17]=[CH:16][NH:15][C:13]=2[N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CI.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Si:1]([NH:8][C:9]1[N:10]=[C:11]([Cl:18])[C:12]2[CH:17]=[CH:16][N:15]([CH3:21])[C:13]=2[N:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22921992HCID 22921992, compound

Product 1

HCID 86665993HCID 86665993, compoundYield 133.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 44.0 g (115.6mmol) of tert-butyldimethylsilylamino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 13.5 ml (1.4 eq.) of methyl iodide in 150 ml of DMF, and 34.40 g (1.6 eq.) of potassium carbonate was reacted at room temperature for 15 hours with vigorous stirring. After addition of water to the reaction mixture, the aqueous solution was extracted with hexane (200 ml×4), washed with brine, and dried over anhydrous magnesium sulfate. The solvents were removed in vacuo, to give 45.87 g (154.5 mmol) (quantitative yield) of 2-ter-butyl-dimethylsilylamino-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine in the form of light yellow crystals. Under nitrogen atmosphere the crystals and 21.19 ml (1.5 eq.) of allyl iodide were dissolved in 300 ml of DMF, and the reaction mixture was cooled to 0° C. with vigorous stirring, then 9.27 g (1.5 eq.) of sodium hydride (60%), thoroughly washed by hexane, was added to that as hexane suspension.

Workup

  1. extractionthe aqueous solution was extracted with hexane (200 ml×4)
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-2407182b5e8449f590345d24698ae0d0
Source dataset
uspto-grants-1997_08
Patent number
US05661148

Reaction notes

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