Tetrahydrofuran → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylmethanesulfonamide

HRID 1668400Notes

Reaction equation

HRID 1668400 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][NH:29][CH3:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:28][N:29]([CH3:30])[S:32]([CH3:31])(=[O:34])=[O:33])=[CH:26][CH:27]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Product 1

HCID 59239862N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylmethanesulfonamideYield 31.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the compound (100 mg) obtained in Example 4, methanesulfonyl chloride (30 mg), triethylamine (76 mg) and tetrahydrofuran (2 ml) was stirred at 0° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The precipitate was collected by filtration to give the title compound (32 mg) as a colorless powder.

Workup

  1. washwashed with water
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fa904f95f59e44b4bcb4103cd33b804a
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

Loading…