Sulfuric Acid → (2R)-2-[[5,6-diamino-2-[[(2-fluorophenyl)methyl]thio]-4-pyrimidinyl]amino]-1-propanol

HRID 968228Notes

Reaction equation

HRID 968228 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[N:15]=[C:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[N:13]=[C:12]([NH:25][C@H:26]([CH3:29])[CH2:27][OH:28])[C:11]=1[N:30]=O.S(=O)(=O)(O)O>O.CN(C=O)C>[NH2:30][C:11]1[C:12]([NH:25][C@H:26]([CH3:29])[CH2:27][OH:28])=[N:13][C:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[N:15][C:10]=1[NH2:9]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 24489Sodium DithioniteHCID 23397118(2R)-2-[[6-amino-2-[[(2-fluorophenyl)methyl]thio]-5-nitroso-4-pyrimidinyl]amino]-1-propanol

Product 1

HCID 69749516(2R)-2-[[5,6-diamino-2-[[(2-fluorophenyl)methyl]thio]-4-pyrimidinyl]amino]-1-propanolYield 12.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium dithionite (4 g) was added in portions to a suspension of the product from example 4, step (d) (8.4 g) in a mixture of water (35 ml) and DMF (15 ml) at 100° C. The resultant yellow solution was cooled in an ice bath and 50% aqueous sulphuric acid (15 ml) was added, giving a grey precipitate. The mixture was stirred for 10 min, then filtered, washing with water, ethanol and diethyl ether, to afford the subtitled product as a grey solid (1.0 g).

Workup

  1. temperatureThe resultant yellow solution was cooled in an ice bath
  2. customgiving a grey precipitate
  3. filtrationfiltered
  4. washwashing with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-23993c89843f4c399e39737b2941f8b0
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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