Dichloromethane → HCID 86713579, compound

HRID 2404038Notes

Reaction equation

HRID 2404038 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16]([S:21]([CH3:24])(=[O:23])=[O:22])=[N:17][CH:18]=3)[N:13]([CH3:25])[C:12]2=[O:26])C=[C:7]([O:9][CH3:10])[CH:8]=1.S(Cl)([Cl:30])(=O)=O.Cl[CH2:33][Cl:34]>>[Cl:30][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:33]([Cl:34])[C:5]=1[N:11]1[CH2:20][C:19]2[C:14](=[N:15][C:16]([S:21]([CH3:24])(=[O:23])=[O:22])=[N:17][CH:18]=2)[N:13]([CH3:25])[C:12]1=[O:26]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24648Sulfuryl chlorideHCID 86713580HCID 86713580, compound

Product 1

HCID 86713579HCID 86713579, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3,5-dimethoxyphenyl)-1-methyl-7-(methylsulfonyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (400 mg, 1.06 mmol) in 15 mL of dichloromethane was added sulfuryl chloride (285 mg, 2.12 mmol) at 0° C., and then stirred at 0° C. for 3 h. LCMS showed the reaction was completed. The reaction mixture was diluted with 20 mL of dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford the title compound (450 mg, 96%) as a yellow solid, which was directly used in the next step without further purification. MS (ES+) C16H16Cl2N4O5S requires: 446, 448. found: 447, 449 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-13a36b0215ac4055a9df5fd390d071ad
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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