Sodium Dithionite → 5,6-Diamino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912680Notes

Reaction equation

HRID 912680 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[C:6](=[S:19])[NH:5][C:4](=[O:20])[CH:3]=1.[N:21]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[NH2:21][C:3]1[C:4](=[O:20])[NH:5][C:6](=[S:19])[N:7]([CH2:8][CH2:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 23668193Sodium NitriteHCID 730143156-Amino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 866311255,6-Diamino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 50.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 6-amino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.55 g, 1.9 mmol, obtained from Example 12(b)) in acetic acid (5 mL) was added, dropwise, a solution of sodium nitrite (0.15 g, 2.1 mmol) in water (1.3 mL). After 50 min, sodium dithionite (0.67 g, 3.8 mmol) was added and the reaction stirred for 20 min, followed by evaporation of acetic acid in vacuo and addition of water (50 mL). The precipitated solid was collected by filtration, washed with water and dried in vacuo, providing the title compound (0.29 g, 50% yield). This material was used in the next step without further purification. MS (ESI)-m/z 303 (M+1).

Workup

  1. customfollowed by evaporation of acetic acid in vacuo and addition of water (50 mL)
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-16d2f3fb8c2c450e9196ef10a99748a9
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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