Methanol → HCID 178456464, compound

HRID 621481Notes

Reaction equation

HRID 621481 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:14]([NH:15][NH2:16])=[CH:13][C:11](=[O:12])[N:10]([CH2:17][CH2:18][CH3:19])[C:8]2=[O:9])=[CH:4][CH:3]=1.[CH3:22][N:23]=[C:24]=S.CO>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:14]3[NH:15][N:16]=[C:22]([NH:23][CH3:24])[C:13]=3[C:11](=[O:12])[N:10]([CH2:17][CH2:18][CH3:19])[C:8]2=[O:9])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11167Methyl isothiocyanateHCID 21243182HCID 21243182, compound

Product 1

HCID 178456464HCID 178456464, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-bromobenzyl)-6-hydrazino-3-propyluracil (4.15 g, 11.8 mM) and methyl isothiocyanate (2.7 ml, 40 mM) in DMF (50 ml) was heated at 120° C. for 24 hours. To the reaction solution was added 50% methanol (15 ml) and the mixture was cooled to give crystals. Recrystallization from DMF/methanol gave colorless needles (2.19 g, 47%), m.p. 308°-310° C.

Workup

  1. temperaturethe mixture was cooled
  2. customto give crystals
  3. customRecrystallization from DMF/methanol

Sources & evidence

ORD record
ord-03154ebc1f4249219606b852b5a3004c
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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