Diisopropylethylamine → HCID 69158921, compound

HRID 2374738Notes

Reaction equation

HRID 2374738 reaction equation
[CH2:1]([C:3]1[C:4](=[O:18])[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[NH:7][CH:8]=1)[CH3:2].I[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([C:3]1[C:4](=[O:18])[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[N:7]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11021060Tert-butyl 2-iodoacetateHCID 178437179HCID 178437179, compound

Product 1

HCID 69158921HCID 69158921, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-2-[2-(4-fluorophenyl)ethyl]-1H-pyrimidin-4-one (B40) (955 mgs) in dichloromethane (20was treated with t-butyl iodoacetate, (2.82 g) and diisopropylethylamine (2.03 mls) at room temperature for 3 days. The solution was washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulphate. The solution was concentrated to give a semi-solid which was triturated with ether:dichloromethane, 5:1, giving the title compound as a white solid, (1.101 g, 79%), 1H-NMR (CDCl3) δ 1.16 (3H, t), 1.47 (9H, s), 2.47 (2H, q), 2.74 (2H, t), 3.14 (2H, t), 4.27 (2H, s), 6.90 (1H, s), 6.98 (2H, m) and 7.17 (2H, m). (APCI+) Found (M+1)=361, C20H25FN3 requires 360.

Workup

  1. washThe solution was washed with saturated sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. concentrationThe solution was concentrated
  4. customto give a semi-solid which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-cc8a0badf96745ef9b28bf875ab40ce1
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

Loading…