Methanesulfonic Acid → N-[2-(N,N-dimethylsulfamoyl)-phenylsulfonyl]-N'-(4-chloromethyl-6-methoxypyrimidin-2-yl)-urea

HRID 542280Notes

Reaction equation

HRID 542280 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH2:15])(=[O:14])=[O:13])(=[O:5])=[O:4].N12CCCN=C1CCCCC2.C1CCN2C(=NCCC2)CC1.[C:39](=O)(OC1C=CC=CC=1)[O:40]C1C=CC=CC=1.CS(O)(=O)=O.[NH2:60][C:61]1[N:66]=[C:65]([CH2:67][Cl:68])[CH:64]=[C:63]([O:69][CH3:70])[N:62]=1>C(#N)C>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:39]([NH:60][C:61]1[N:66]=[C:65]([CH2:67][Cl:68])[CH:64]=[C:63]([O:69][CH3:70])[N:62]=1)=[O:40])(=[O:14])=[O:13])(=[O:5])=[O:4]

Participants

7

Reactant 5

HCID 6395Methanesulfonic AcidHCID 7597Diphenyl carbonateHCID 13371850N1,N1-dimethylbenzene-1,2-disulfonamideHCID 138848154-(Chloromethyl)-6-methoxypyrimidin-2-amineHCID 673932131,8-diazabicyclo(5,4,0)undec-7-ene DBU

Product 1

HCID 13884816N-[2-(N,N-dimethylsulfamoyl)-phenylsulfonyl]-N'-(4-chloromethyl-6-methoxypyrimidin-2-yl)-ureaYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

26.4 g of 2-(N,N-dimethylsulfamoyl)-benzenesulfonamide (0.1 mol) are suspended in 100 ml of acetonitrile; 15.7 g of 1,8-diazabicyclo(5,4,0)undec-7-ene DBU (0.1 mol) are added, and the mixture is stirred for 1 hour at room temperature. There are then added 21.4 g of diphenyl carbonate (0.1 mol) and stirring is continued for 1 hour. After a standing time of 15 hours, 9.7 g of methanesulfonic acid (0.1 mol) are added dropwise in the cold state. There are afterwards added 17.3 g of 2-amino-4-chloromethyl-6-methoxypyrimidine (0.1 mol), and the suspension is refluxed for 1 hour, in the course of which there is firstly formed a solution from which, after a short time, the product precipitates in crystalline form. The reaction mixture is cooled and the product is filtered off under suction to thus obtain 32 g of slightly yellowish product; m.p. 214°-216° C. (decomp.); yield 70% of theory.

Workup

  1. stirringstirring
  2. waitis continued for 1 hour
  3. temperaturethe suspension is refluxed for 1 hour, in the course of which there
  4. customis firstly formed a solution from which
  5. customafter a short time, the product precipitates in crystalline form
  6. temperatureThe reaction mixture is cooled
  7. filtrationthe product is filtered off under suction to thus obtain 32 g of slightly yellowish product

Sources & evidence

ORD record
ord-87929dbfb8b846df80d441485342345a
Source dataset
uspto-grants-1987_04
Patent number
US04656273

Reaction notes

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