1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19899627, compound

HRID 1029327Notes

Reaction equation

HRID 1029327 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12](=[O:20])OC2C=CC=CC=2)[N:4]=1.[S:21](=[O:36])(=[O:35])([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][CH2:32][O:33][CH3:34])[NH2:22].N12CCCN=C1CCCCC2>C(#N)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([NH:11][C:12](=[O:20])[NH:22][S:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][CH2:32][O:33][CH3:34])(=[O:36])=[O:35])[N:6]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 19899629HCID 19899629, compound

Product 1

HCID 19899627HCID 19899627, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.74 g (0.0063 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate are dissolved in 80 ml of acetonitrile, and 1.48 g (0.006 mol) of 2-(2-methoxyethoxy)phenyl sulfamate are added at room temperature. 1.0 g (0.0066 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added and the reaction mixture is then stirred at room temperature for 18 hours, concentrated, diluted with H2O and acidified with 2N hydrochloric acid to give a pH of 3-4. After the solids have been filtered off with suction and dried, 2.4 g (93% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)phenoxysulfonyl]urea of melting point 106°-108° C. are obtained.

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O
  3. customto give a pH of 3-4
  4. filtrationAfter the solids have been filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-dc26122cd5514a3286cd99d79fa01a78
Source dataset
uspto-grants-1992_04
Patent number
US05102443

Reaction notes

Loading…