Methanol → N-[6-(3-Hydroxymethyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 2069200Notes

Reaction equation

HRID 2069200 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[N+:18]([O-:20])=[O:19])[NH:14][C:13](=[O:21])[N:12]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:11]3=[O:27])[CH:4]=1)=[O:2].CO>C(O)(=O)C>[OH:2][CH2:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[N+:18]([O-:20])=[O:19])[NH:14][C:13](=[O:21])[N:12]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:11]3=[O:27])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 11574709N-[6-(3-Formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

Product 1

HCID 11509452N-[6-(3-Hydroxymethyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-[6-(3-formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (580 mg, 1.47 mmol, crude from previous step) in methanol (5 ml) sodium borohydride (112 mg, 2.95 mmol) is added at 0° C. and allowed to stir for 30 minutes. A small quantity of acetic acid is added to destroy excess sodium borohydride. The reaction mixture is diluted with ethyl acetate and washed two times with water and the solvent of the organic layer is removed by rotavapor evaporation to give a red-brown oil which is purified by flash chromatography with DCM/methanol from 98:2 to 95:5 to yield the title compound as an orange solid, m.p. 250-270° C. (decomp.).

Workup

  1. customto destroy excess sodium borohydride
  2. additionThe reaction mixture is diluted with ethyl acetate
  3. washwashed two times with water
  4. customthe solvent of the organic layer is removed by rotavapor evaporation
  5. customto give a red-brown oil which
  6. customis purified by flash chromatography with DCM/methanol from 98:2 to 95:5

Sources & evidence

ORD record
ord-8391dcbdd6fc4de59cb74602a4f4d003
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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