1-Butanesulfonyl chloride → HCID 59834685, compound

HRID 271623Notes

Reaction equation

HRID 271623 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[C:21](=[O:22])[CH2:20][NH:19][CH2:18][C:17]1=[O:23].[CH2:26]([S:30](Cl)(=[O:32])=[O:31])[CH2:27][CH2:28][CH3:29]>N1C=CC=CC=1.C(Cl)Cl>[CH2:26]([S:30]([N:19]1[CH2:18][C:17](=[O:23])[N:16]([CH2:15][C:5]2[N:4]([CH2:3][C:2]([CH3:25])([CH3:24])[CH3:1])[C:8]3[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=3[CH:6]=2)[C:21](=[O:22])[CH2:20]1)(=[O:32])=[O:31])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 754301-Butanesulfonyl chlorideHCID 59834656HCID 59834656, compound

Product 1

HCID 59834685HCID 59834685, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.59 mmoles) of 7-(2,2-dimethyl-propyl)-6-(2,6-dioxo-piperazin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 4 ml of pyridine, 184 mg (1.2 mmoles) of 1-butanesulfonylchloride is added at 0° C. The reaction mixture is allowed to warm to ambient temperature and stirred for 2 hours and the mixture is concentrated under reduced pressure. The obtained crude powder is dissolved in CH2Cl2, and the CH7Cl2 layer is washed with 1N aqueous HCl, brine, and then dried over MgSO4. The CH2Cl2 layer is concentrated under reduced pressure to give colorless powder, which is washed with ether to give 195 mg of desred 6-[4-(Butane-1-sulfonyl)-2,6-dioxo-piperazin-1-ylmethyl]-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 72% yield.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customThe obtained crude powder
  3. washthe CH7Cl2 layer is washed with 1N aqueous HCl, brine
  4. dry with materialdried over MgSO4
  5. concentrationThe CH2Cl2 layer is concentrated under reduced pressure
  6. customto give colorless powder, which
  7. washis washed with ether

Sources & evidence

ORD record
ord-84b8c39fe78642de9ae87a9c80ace4b9
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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