4-Fluorobenzylic alcohol → HCID 59514509, compound

HRID 2422168Notes

Reaction equation

HRID 2422168 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 tetrahydrofuran (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-aca0019bddbf4c0c9031d582460e6f86
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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