Dabco → N-[(5,6-Dihydro-4-methylfuro(2,3-d)pyrimidin-2-yl)-aminocarbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide

HRID 1252856Notes

Reaction equation

HRID 1252856 reaction equation
[CH3:1][C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.N12CCN(CC1)CC2.[CH3:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])[C:24]=2[N:23]=[N:22]1>C(#N)C.O>[CH3:1][C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH:8][C:34]([NH:33][S:30]([C:29]2[C:24]3[N:23]=[N:22][N:21]([CH3:20])[C:25]=3[CH:26]=[CH:27][CH:28]=2)(=[O:31])=[O:32])=[O:35])[N:7]=1

Participants

6

Reactant 3

HCID 9237DabcoHCID 40988324-Methyl-5,6-dihydrofuro[2,3-d]pyrimidin-2-amineHCID 141800421-Methyl-1H-benzotriazole-4-sulfonylisocyanate

Product 1

HCID 14180045N-[(5,6-Dihydro-4-methylfuro(2,3-d)pyrimidin-2-yl)-aminocarbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 5,6-dihydro-4-methylfuro(2,3-d)pyrimidin-2-amine (0.08 g) and 1,4-diazabicyclo[2,2,2]octane (catalytic amount) in acetonitrile (5 mL) was added 0.125M 1-methyl-1H-benzotriazole-4-sulfonylisocyanate in acetonitrile (4.0 mL) under a nitrogen atmosphere. After stirring for 4 hours, the reaction was diluted with water (20 mL) and the precipitate was filtered, washed with water and ether, and dried to give 0.09 g of the title compound as a white solid. m.p. 234°-240° C. with decomposition.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water and ether
  3. customdried

Sources & evidence

ORD record
ord-b2ee45c6c73d4582b5edc4e1015c3675
Source dataset
uspto-grants-1988_05
Patent number
US04746356

Reaction notes

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