Diisopropylethylamine → 2-(2-Chloro-6-[3-trimethylsilylpropyl]pyrimidin-4-ylamino)-4-methyl-pentanoic acid (3-ethoxypropyl)amide

HRID 1822816Notes

Reaction equation

HRID 1822816 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=1.Cl.[CH2:17]([O:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:26])[CH3:18].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:17]([O:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:31])[CH:25]([NH:26][C:6]1[CH:5]=[C:4]([CH2:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=[C:2]([Cl:1])[N:7]=1)[CH2:27][CH:28]([CH3:29])[CH3:30])[CH3:18]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 221700372,4-Dichloro-6-[3-(trimethylsilyl) propyl]pyrimidineHCID 23568571L-leucine-3-ethoxypropylamide hydrochloride

Product 1

HCID 235685982-(2-Chloro-6-[3-trimethylsilylpropyl]pyrimidin-4-ylamino)-4-methyl-pentanoic acid (3-ethoxypropyl)amideYield 58.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-dichloro-6-[3-(trimethylsilyl)-propyl]pyrimidine (1 gram), L-leucine-3-ethoxypropylamide hydrochloride (1 gram) and N,N-diisopropylethylamine (2.3 mL) were stirred for 17 h in 20 mL dimethyl sulfoxide at 55° C. The solution was cooled to room temperature and diluted with ethyl acetate (100 mL), then washed 4 times with 100 mL aliquots of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered, and the solvents were removed in vacuo. Silica gel chromatography (heptane/ethyl acetate 3/1) provided 978 mg of 2-(2-chloro-6-[3-trimethylsilylpropyl]pyrimidin-4-ylamino)-4-methyl-pentanoic acid (3-ethoxypropyl)amide.

Workup

  1. washwashed 4 times with 100 mL aliquots of a saturated aqueous solution of sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-3ad2f73b16b54d8b8ddb16683b001be0
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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