4-Fluorobenzyl bromide → HCID 18540813, compound

HRID 411287Notes

Reaction equation

HRID 411287 reaction equation
[CH2:1]([N:12]1[CH:19]=[C:18]([CH2:20][C:21]2[CH:22]=[N:23][C:24]([O:27][CH2:28][CH3:29])=[N:25][CH:26]=2)[C:16](=[O:17])[NH:15][C:13]1=[S:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(N(C(C)C)CC)(C)C.[F:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([N:12]1[CH:19]=[C:18]([CH2:20][C:21]2[CH:22]=[N:23][C:24]([O:27][CH2:28][CH3:29])=[N:25][CH:26]=2)[C:16](=[O:17])[N:15]=[C:13]1[S:14][CH2:44][C:43]1[CH:46]=[CH:47][C:40]([F:39])=[CH:41][CH:42]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 81531DiisopropylethylamineHCID 18540810HCID 18540810, compound

Product 1

HCID 18540813HCID 18540813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-undecyl-5-(2-ethoxypyrimidin-5-ylmethyl)-2-thiouracil (5.0 g) and diisopropylethylamine (2.1 ml) in dry methylene chloride (200 ml) was added 4-fluorobenzyl bromide (1.5 ml) and the mixture stirred under argon at room temperature for 20 h. The solution was washed with 5% aqueous sodium bicarbonate and the organic layer was added directly to a silica gel column (200 g). Elution with ethyl acetate to 5% methanol in ethyl acetate gave the desired product (2.7 g). 1H-NMR (CDCl3) δ0.8-0.95 (3H,m), 1.15-1.4 (16H,m), 1.43 (3H,t), 1.55-1.8 (2H,m), 3.68 (2H,s), 3.71 (2H,t), 4.41 (2H,q), 4.47 (2H,s), 6.86 (1H,s), 6.9-7.1 (2H,m), 7.3-7.45 (2H,m), 8.45 (2H,d); MS (APCI+) found (M+1)=527; C29H39FN4O2S requires 526.

Workup

  1. washThe solution was washed with 5% aqueous sodium bicarbonate
  2. additionthe organic layer was added directly to a silica gel column (200 g)
  3. washElution with ethyl acetate to 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-a10088f48ea248d182498c6c55caa809
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

Loading…