Phosphoric Acid → HCID 21998636, compound

HRID 1976557Notes

Reaction equation

HRID 1976557 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[C:6](=[S:25])[NH:5][C:4](=[O:26])[CH:3]=1.P(=O)(O)(O)O.[N:32]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CS(C)=O.C1COCC1.O.CO>[CH2:18]([O:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[CH2:8][N:7]1[C:2]([NH2:1])=[C:3]([NH2:32])[C:4](=[O:26])[NH:5][C:6]1=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 1004Phosphoric AcidHCID 24489Sodium DithioniteHCID 21998640HCID 21998640, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21998636HCID 21998636, compoundYield 105.6%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

6-amino-1-(3-benzyloxy-4-methoxy-benzyl)-2-thiouracil (36.94 g, 100 mmole) was dissolved in DMSO (74 ml), diluted with THF (185 ml) and treated with 85% phosphoric acid (7.46 ml). At 55-60° C., 4M sodium nitrite (30 ml, 120 mmole) was added slowly. After 30 minutes, methanol (10 ml) was added, the reaction was cooled to 30° C., and a suspension of 85% sodium dithionite (40.96 g, 200 mmole) in water (80 ml) was added slowly. After the addition of water (200 ml) the solvent was removed in vacuo and the suspension diluted with water to 1 l. The solid was collected at 0-5° C. to give crude 1-(3-benzyloxy-4-methoxy-benzyl)-5,6-diamino-2-thiouracil (40.58 g).

Workup

  1. additionwas added slowly
  2. customwas removed in vacuo
  3. additionthe suspension diluted with water to 1 l
  4. customThe solid was collected at 0-5° C.

Sources & evidence

ORD record
ord-05dd7cdb56884f718e51d83ff574f2ff
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

Loading…