Benzyl Alcohol → HCID 12559160, compound

HRID 1742754Notes

Reaction equation

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([Cl:19])[N:13]=1.[OH2:20]>O1CCCC1>[CH2:1]([O:8][C:12]1[N:17]=[C:16]([O:20][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[C:14]([Cl:19])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The reaction is carried out under an argon protective-gas atmosphere. 24.8 ml (0.24 mol) of absolute benzyl alcohol in 100 ml of THF are added dropwise at 25° C. to 9.6 g of NaH (0.24 mol, 60% suspension in paraffin) in 120 ml of tetrahydrofuran (THF). The reaction mixture is warmed at 50° C. for 0.5 hour, cooled and then added dropwise to a solution, cooled to 0° C., of 13.8 ml of 2,4,6-trichloropyrimidine in 100 ml of THF. The mixture is allowed to warm to 25° C. overnight, and is then poured into 200 ml of water. After extraction with toluene three times, the combined organic phases are washed with 100 ml of water, dried using MgSO4, filtered and evaporated on a rotary evaporator. Filtration through silica gel (eluent ethyl acetate:hexane 1:1) gives 39.9 g (100% of theory) of the title product.

Workup

temperaturecooled
additionadded dropwise to a solution
temperatureto warm to 25° C. overnight
extractionAfter extraction with toluene three times
washthe combined organic phases are washed with 100 ml of water
customdried
filtrationfiltered
customevaporated on a rotary evaporator
filtrationFiltration through silica gel (eluent ethyl acetate:hexane 1:1)

Sources & evidence

ORD record: ord-7bc5a0a9e20f44aa94b1fa28abb5cc23
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340701

Reaction notes

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