Sodium hydride → 4-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51482

Reaction equation

HRID 51482 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[H][H].S(O[CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:27]3[CH2:31][CH2:30][O:29][CH2:28]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 178418361HCID 178418361, compound

Product 1

HCID 227364154-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.0 g) was added to a mixture of sodium hydride (0.79 g of a 60% dispersion in mineral oil) in dimethylformamide (100 ml) with stirring under nitrogen at 0° C. The mixture was stirred until hydrogen evolution ceased. 3-Tosyloxytetrahydrofuran (4.65 g) was added at 0° C. and then the mixture was warmed to 90° C. The mixture was stirred at this temperature for 2 hours and then overnight at ambient temperature. Water (100 ml) was added cautiously and the mixture was extracted with ethyl acetate to give 4-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine, m.p. 184-186° C.

Workup

  1. temperaturethe mixture was warmed to 90° C
  2. stirringThe mixture was stirred at this temperature for 2 hours
  3. customovernight
  4. customat ambient temperature
  5. extractionthe mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-42cab23401b141169cdb7e9ba9557641
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

Loading…