4-Toluenesulfonyl chloride → 2,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

HRID 2046992Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

503 mg 2,4-dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (5) (2.5 mmol) and 523 mg TsCl (2.75 mmol) were dissolved in 20 mL of DMF. After cooling to 0° C., 200 mg NaH (2.75 mmol) was slowly added under N2. The reaction mixture was stirred at 0° C. for 30 minutes and quenched by adding 10 mL of 10% aqueous NH4Cl at this temperature, then extracted with EtOAc (3×50 mL). Combined organic layers were washed with brine, dried over Na2SO4 and purified by flash column chromatography to give the title compound as light yellow solid.

Workup

customquenched
additionby adding 10 mL of 10% aqueous NH4Cl at this temperature
extractionextracted with EtOAc (3×50 mL)
washCombined organic layers were washed with brine
dry with materialdried over Na2SO4
custompurified by flash column chromatography

Sources & evidence

ORD record: ord-f644aa95376942b6b6f3e4852a135056
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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