Acetone → HCID 60204670, compound

HRID 507691Notes

Reaction equation

HRID 507691 reaction equation
[Br:1][C:2]1[C:3]([C:20]2[S:28][C:27]3[CH2:26][CH2:25][NH:24][CH2:23][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.[CH3:29][C:30]([CH3:32])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[Br:1][C:2]1[C:3]([C:20]2[S:28][C:27]3[CH2:26][CH2:25][N:24]([CH:30]([CH3:32])[CH3:29])[CH2:23][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 60204673HCID 60204673, compound

Product 1

HCID 60204670HCID 60204670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-(5-Bromo-4-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (0.15 g, 032 mmol) was treated with acetone (1 mL), sodium triacetoxyborohydride (0.136 g, 0.64 mmol) in dicholoethane (5 mL). The reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and water. The layers were separated and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine. The mixture was dried with sodium sulfate and purified by preparative HPLC. Yield=0.05 g. MS (M+H)+ 507/509.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  3. dry with materialThe mixture was dried with sodium sulfate
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c31b9b51bac54889ad94ec42f902bf20
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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