Sodium borohydride → 1-(9-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-3-(2-hydroxyethyl)urea

HRID 1912837Notes

Reaction equation

HRID 1912837 reaction equation
[CH2:1]([NH:4][C:5]([NH:7][C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=2)=[O:25])=[CH:19][CH:18]=1)=[O:6])[CH:2]=C.I([O-])(=O)(=O)=[O:39].[Na+].[BH4-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:24](=[O:25])[NH:23][C:20]2[CH:21]=[CH:22][C:17]([N:12]3[CH:11]=[N:10][C:9]4[C:13]3=[N:14][CH:15]=[N:16][C:8]=4[NH:7][C:5]([NH:4][CH2:1][CH2:2][OH:39])=[O:6])=[CH:18][CH:19]=2)=[CH:28][C:29]=1[C:34]([F:37])([F:36])[F:35]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 231550851-Allyl-3-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)ureaHCID 23667635Sodium periodate

Product 1

HCID 231551081-(9-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-3-(2-hydroxyethyl)ureaYield 13%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solution of 3 mL of tetrahydrofuran and 1 mL of water, 50 mg (0.09 mmol) of 1-allyl-3-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)urea was dissolved, and 19 μL of a 0.1 M osmium tetraoxide aqueous solution and 81 mg (0.19 mmol) of sodium periodate were added thereto and the mixture solution was stirred at room temperature for three hours. The reaction solution was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was dissolved in 2 mL of ethanol, and 5 mg (0.13 mmol) of sodium borohydride was added thereto and the mixture solution was stirred at room temperature for one hour. The reaction solution was concentrated, and purified by a silica gel column (dichloromethane:methanol=9:1) to obtain 5 mg (13%) of a target product as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 2 mL of ethanol
  6. stirringthe mixture solution was stirred at room temperature for one hour
  7. concentrationThe reaction solution was concentrated
  8. custompurified by a silica gel column (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-1f6b761a04a14322bf1cc9172be1c874
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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