2-Bromopropane → HCID 492813, compound

HRID 1637714Notes

Reaction equation

HRID 1637714 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[N:3]=1.[OH-].[K+].Br[CH:21]([CH3:23])[CH3:22]>CS(C)=O>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH:21]([CH3:23])[CH3:22])[CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 15550151HCID 15550151, compound

Product 1

HCID 492813HCID 492813, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-amino-6-chloro-2-(3-hydroxyphenylmethylthio)-pyrimidine (135 mg, 0.50 mmol; Cpd 108) is added to a solution of KOH (280 mg, 5 mmol) in DMSO (2.5 ml) at room temperature. 2-Bromopropane (615 mg, 5 mmol) is added and the reaction stirred overnight, then poured onto water. The aqueous solution is extracted with ethyl acetate, dried with MgSO4, filtered, and concentrated in vacuo. The sample is purified by chromatography using 1:3 ethyl acetate/hexanes, mp 71° C.

Workup

  1. additionpoured onto water
  2. extractionThe aqueous solution is extracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe sample is purified by chromatography

Sources & evidence

ORD record
ord-f56b4e6120ea4dfca7e747841bac28ef
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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