Water → HCID 59286185, compound

HRID 1957996Notes

Reaction equation

HRID 1957996 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:23]=[CH:22][C:21]3[N:20]([CH3:24])[C:19](=[O:25])[CH2:18][N:17]([CH:26]([CH3:28])[CH3:27])[C:16]=3[N:15]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5].C(N(C(C)C)C(C)C)C.[S:38](Cl)([CH3:41])(=[O:40])=[O:39].O>ClCCl.CN(C)C1C=CN=CC=1>[CH:26]([N:17]1[C:16]2[N:15]=[C:14]([NH:13][C:9]3[CH:8]=[C:7]([S:4]([CH2:3][CH2:2][O:1][S:38]([CH3:41])(=[O:40])=[O:39])(=[O:5])=[O:6])[CH:12]=[CH:11][CH:10]=3)[N:23]=[CH:22][C:21]=2[N:20]([CH3:24])[C:19](=[O:25])[CH2:18]1)([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59286160HCID 59286160, compound

Product 1

HCID 59286185HCID 59286185, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-(2-Hydroxyethylsulfonyl)phenylamino)-8-isopropyl-5-methyl-7,8-dihydropteridin-6(5H)-one (1.45 g; 3.576 mmol) was dissolved in 35 mL dichloromethane, ethyldiisopropylamine (0.92 mL; 5.360 mmol) and 4-dimethylaminopyridine (cat.) were added. Then the mixture was cooled to 0° C. and mesylchloride (0.332 ml; 4.290 mmol) was added slowly. The reaction mixture was allowed to get to room temperature and after 4 h water was added and the mixture was extracted with dichloromethane. Drying of the organic layer with sodium sulphate and removal of the solvents gave 1.1 g (2.275; 63% yield) of intermediate the desired product as foam.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialDrying of the organic layer with sodium sulphate and removal of the solvents

Sources & evidence

ORD record
ord-32cc40a76f4d444b8e5400b3ab1dd2fa
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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