Dimethylformamide → HCID 178440253, compound

HRID 1663312Notes

Reaction equation

HRID 1663312 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[N:11]=[C:10]([OH:17])[N:9]=2)=[CH:4][CH:3]=1.CN(C=O)C.[Br:23]N1C(=O)CCC1=O>O>[Br:23][C:13]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][C:10]([OH:17])=[N:11][C:12]=1[CH:14]([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 178438788HCID 178438788, compound

Product 1

HCID 178440253HCID 178440253, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-3 °C

Procedure

4-(4-Fluorophenyl)-6-isopropylpyrimidin-2-ol (8.00 g, 34.1 mmol) was charged to a reactor followed by DMF (100 mL). The suspension was stirred, cooled to −3° C. and N-bromosuccinimide (6.25 g, 34.8 mmol) added. The reaction mixture was warmed to 20° C. and stirred overnight. Water (100 mL) was charged to the reaction mixture and the crystalline mixture stirred for 1 hour before filtering off. The isolated solid was washed twice with water (25 mL) and the solid dried in a vacuum oven at 50° C. 5-Bromo-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-ol (10.45 g, 97% yield) was obtained as a white solid;

Workup

  1. temperatureThe reaction mixture was warmed to 20° C.
  2. stirringstirred overnight
  3. stirringthe crystalline mixture stirred for 1 hour
  4. filtrationbefore filtering off
  5. washThe isolated solid was washed twice with water (25 mL)
  6. customthe solid dried in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-ad287b19904a4e6e968c228370193e93
Source dataset
uspto-grants-2011_10
Patent number
US08034932B2

Reaction notes

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