Dichloromethane → 4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1926690Notes

Reaction equation

HRID 1926690 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](C=CC=1C)[C:5]([NH:7][C:8]1C=CC(CN2CCN(CC)CC2)=C(C(F)(F)F)C=1)=O.C([N:33](CC)CC)C.[S:38](Cl)([C:41]1[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=1)(=[O:40])=[O:39].Cl[CH2:50][Cl:51]>CN(C)C1C=CN=CC=1>[Cl:51][C:50]1[C:4]2[CH:3]=[CH:2][N:1]([S:38]([C:41]3[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[C:5]=2[N:7]=[CH:8][N:33]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59346397HCID 59346397, compound

Product 1

HCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Into a solution of 6-chloro deazapurine (4, 10.0 g, 65 mmol, 1.0 eq.) in dichloromethane (325 ml) are added triethylamine (9.9 ml, 71.5 mmol, 1.1 eq.) and 4-dimethylamino pyridine (catalytic). Tosyl chloride (12.76 g, 66.9 mmol, 1.03 eq.) is added in portions into the reaction mixture which is further equilibrated for 30 minutes. The reaction mixture is then partitioned between dichloromethane and water. The organic layer is separated and the aqueous layer is extracted with dichloromethane. The combined organic extracts are washed with water, dried over Na2SO4, filtered and concentrated to afford the title product which is used in the next step without further purification.

Workup

  1. customThe reaction mixture is then partitioned between dichloromethane and water
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with dichloromethane
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7030669ae3a49a9a23da809a8977694
Source dataset
uspto-grants-2012_05
Patent number
US08183248B2

Reaction notes

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