Sodium Bicarbonate → HCID 178448291, compound

HRID 1182054Notes

Reaction equation

HRID 1182054 reaction equation
[Br:1][C:2]1[C:3]([NH:16][C@H:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][OH:19])=[N:4][C:5]([NH:8][C:9]2[NH:13][C:12]([S:14][CH3:15])=[N:11][N:10]=2)=[N:6][CH:7]=1.C([O-])(O)=[O:24].[Na+].OOS([O-])=O.[K+]>CO.O.O>[Br:1][C:2]1[C:3]([NH:16][C@H:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][OH:19])=[N:4][C:5]([NH:8][C:9]2[NH:13][C:12]([S:14]([CH3:15])=[O:24])=[N:11][N:10]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite2×HCID 178503617HCID 178503617, compound

Product 1

HCID 178448291HCID 178448291, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

At 0° C., 159 mg (0.41 mmol) of (R)-2-[5-bromo-2-(5-methylsulfanyl-4H-[1,2,4]triazol-3-ylamino)-pyrimidin-4-ylamino]-3-methyl-butan-1-ol in 4 ml of MeOH/water (4:1) is mixed with 80 mg (0.95 mmol) of NaHCO3 and 98 mg (0.95 mmol) of oxone. The reaction mixture is stirred for 2 hours at room temperature, then another 50 mg (0.5 mmol) of oxone is added, and it is stirred for 1 hour at 30° C. The batch is diluted with water and extracted with ethyl acetate. The organic phase is concentrated by evaporation and purified by chromatography (methylene chloride-(methylene chloride/ethanol: 9/1); Flashmaster II). After the recrystallization, 45 mg (0.11 mmol, 27% of theory) of the product (R)-2-[5-bromo-2-(5-methanesulfinyl-4H-[1,2,4]triazol-3-ylamino)-pyrimidin-4-ylamino]-3-methyl-butan-1-ol is obtained.

Workup

  1. stirringit is stirred for 1 hour at 30° C
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic phase is concentrated by evaporation
  4. custompurified by chromatography (methylene chloride-(methylene chloride/ethanol: 9/1); Flashmaster II)
  5. customAfter the recrystallization, 45 mg (0.11 mmol, 27% of theory) of the product (R)-2-[5-bromo-2-(5-methanesulfinyl-4H-[1,2,4]triazol-3-ylamino)-pyrimidin-4-ylamino]-3-methyl-butan-1-ol
  6. customis obtained

Sources & evidence

ORD record
ord-7657b7a0d67d4ba6bc1183af2e2ddd96
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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