4-Chlorobenzyl alcohol → HCID 45275190, compound

HRID 1942897Notes

Reaction equation

HRID 1942897 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Na].Cl[C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([O:33][CH3:34])[CH:22]=2)[N:13]=1>O1CCCC1.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]4)=[C:23]([O:33][CH3:34])[CH:22]=3)[N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 133974-Chlorobenzyl alcoholHCID 5360545Sodium2×HCID 86640783(4-Chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

Product 1

HCID 45275190HCID 45275190, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chlorobenzyl alcohol (45 mg, 0.32 mmol) in 10 ml of tetrahydrofuran was added metallic sodium (7 mg, 0.30 mmol). The mixture was stirred until the sodium dissolved. (4-Chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (100 mg, 0.29 mmol) was added and the mixture refluxed for 4 hours, diluted with water and extracted with ethyl acetate. The product was purified by chromatography on Si—NH2 (Isolute) using ethyl acetate as a solvent to give the title compound (26 mg, 20%) as a colorless solid.

Workup

  1. dissolutiondissolved
  2. temperaturethe mixture refluxed for 4 hours
  3. extractionextracted with ethyl acetate
  4. customThe product was purified by chromatography on Si—NH2 (Isolute)

Sources & evidence

ORD record
ord-2445a5d7969c48dd808e2d3eac5d7d52
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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