2-Bromopropane → HCID 492813, compound

HRID 1602184Notes

Reaction equation

HRID 1602184 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-23732e7ba58940939cdabab57e78632e
Source dataset
uspto-grants-1999_11
Patent number
US05981537

Reaction notes

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