4-Fluorobenzylic alcohol → HCID 59514509, compound

HRID 1159681Notes

Reaction equation

HRID 1159681 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][N:6]=[C:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24]C3C=CC=CC=3)=[O:23])=[CH:17][CH:16]=2)[N:4]=1.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]O)=[CH:35][CH:34]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:31])[C:3]1[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][N:6]=[C:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:37][C:36]3[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=3)=[O:23])=[CH:17][CH:16]=2)[N:4]=1

Participants

5

Reactant 3

HCID 680224-Fluorobenzylic alcoholHCID 81531DiisopropylethylamineHCID 59514548HCID 59514548, compound

Product 1

HCID 59514509HCID 59514509, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl (4-(dimethylamino)-2-{4-[(phenoxycarbonyl)amino]benzyl}pyrimidin-5-yl)acetate (100 mg, 0.24 mmol) and 4-fluorobenzyl alcohol (60 mg, 0.48 mmol) in N,N-diisopropylethylamine (0.17 mL, 0.95 mmol) and tetrahydofuran (2 mL) was refluxed for 24 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the remaining residue was purified by preparative TLC (chloroform/methanol 30:1) to give methyl {4-(dimethylamino)-2-[4-({[(4-fluorobenzyl)oxy]carbonyl}amino)benzyl]pyrimidin-5-yl}acetate (45 mg, 42%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe remaining residue was purified by preparative TLC (chloroform/methanol 30:1)

Sources & evidence

ORD record
ord-847c72c783594047842525962c9bd493
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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