Sodium borohydride → 2-(Diaminomethyleneamino)-4-(5-hydroxymethylpyridin-3-yl)thiazole

HRID 1491894Notes

Reaction equation

HRID 1491894 reaction equation
[BH4-].[Na+].[NH2:3][C:4](=[N:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18](OC)=[O:19])[CH:17]=2)[N:11]=1)[NH2:5]>O.CO.O1CCCC1>[NH2:3][C:4](=[N:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][OH:19])[CH:17]=2)[N:11]=1)[NH2:5]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 104687342-(Diaminomethyleneamino)-4-(5-methoxycarbonylpyridin-3-yl)thiazole

Product 1

HCID 100606192-(Diaminomethyleneamino)-4-(5-hydroxymethylpyridin-3-yl)thiazoleYield 45.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium borohydride (1.2 g) in water (25 ml) was added slowly to a solution of 2-(diaminomethyleneamino)-4-(5-methoxycarbonylpyridin-3-yl)thiazole (2.8 g) in methanol (70 ml) and tetrahydrofuran (70 ml) under refluxing for 20 minutes. The mixture was refluxed for 4 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (100 ml). The mixture was extracted with a mixture of ethyl acetate (300 ml) and tetrahydrofuran (150 ml). The extract was dried with magnesium acetate and then evaporated to afford 2-(diaminomethyleneamino)-4-(5-hydroxymethylpyridin-3-yl)thiazole (1.14 g).

Workup

  1. temperatureunder refluxing for 20 minutes
  2. temperatureThe mixture was refluxed for 4 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water (100 ml)
  5. extractionThe mixture was extracted with a mixture of ethyl acetate (300 ml) and tetrahydrofuran (150 ml)
  6. dry with materialThe extract was dried with magnesium acetate
  7. customevaporated

Sources & evidence

ORD record
ord-edf8187e6ae346f6bb01e378927aa302
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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