Sodium Dithionite → 5,6-diamino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912666Notes

Reaction equation

HRID 912666 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)[C:6](=[S:18])[NH:5][C:4](=[O:19])[CH:3]=1.[N:20]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[NH2:20][C:3]1[C:4](=[O:19])[NH:5][C:6](=[S:18])[N:7]([CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)[C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 23668193Sodium NitriteHCID 866311166-amino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 866311185,6-diamino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 65.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 6-amino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.28 g, 1.0 mmol, obtained from Example 8(b)) in acetic acid (3 mL) was added, dropwise, a solution of sodium nitrite (0.080 g, 1.1 mmol) in H2O (0.5 mL). The reaction mixture was then stirred for an additional 40 minutes before sodium dithionite (0.36 g, 2.08 g) was added. The resulting mixture was stirred 15 minutes and then evaporated in vacuo. Water (50 mL) was added and the formed solid was collected by filtration, washed with water and dried which gave the title compound (0.19 g, 63%).

Workup

  1. additionwas added
  2. additionwas added
  3. customevaporated in vacuo
  4. additionWater (50 mL) was added
  5. filtrationthe formed solid was collected by filtration
  6. washwashed with water
  7. customdried which

Sources & evidence

ORD record
ord-20bd877600d841bba99460973ff42ab3
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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