Sodium Nitrite → (2R)-2-[[6-amino-2-[[(2-fluorophenyl)methyl]thio]-5-nitroso-4-pyrimidinyl]amino]-1-propanol

HRID 968227Notes

Reaction equation

HRID 968227 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:5]=[C:4]([NH:17][C@H:18]([CH3:21])[CH2:19][OH:20])[CH:3]=1.[N:22]([O-])=[O:23].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:5]=[C:4]([NH:17][C@H:18]([CH3:21])[CH2:19][OH:20])[C:3]=1[N:22]=[O:23]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 69750714HCID 69750714, compound

Product 1

HCID 23397118(2R)-2-[[6-amino-2-[[(2-fluorophenyl)methyl]thio]-5-nitroso-4-pyrimidinyl]amino]-1-propanolYield 43.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product from example 4, step (c) (10 g) in acetic acid (300 ml) at room temperature was added a solution of sodium nitrite (2.24 g) in water (30 ml). The reaction was stirred at 0° C. for 30 min, and the resultant purple precipitate isolated by filtration, washing with water, to give the subtitled compound as a dark blue solid (4.8 g).

Workup

  1. customthe resultant purple precipitate isolated by filtration
  2. washwashing with water

Sources & evidence

ORD record
ord-e63308adf16047309f44b6a265e4f4dd
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

Loading…