Methanol → 3-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1994407Notes

Reaction equation

HRID 1994407 reaction equation
C[Si](I)(C)C.C(OC(=O)[NH:15][CH:16]1[C:21](=[O:22])[N:20]2[CH:23]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[C:24](=[O:30])[N:25]([CH:27]([CH3:29])[CH3:28])[CH2:26][CH:19]2[N:18]([S:39]([C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=2[Cl:49])(=[O:41])=[O:40])[CH2:17]1)C1C=CC=CC=1.CO>CC#N>[NH2:15][CH:16]1[C:21](=[O:22])[N:20]2[CH:23]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[C:24](=[O:30])[N:25]([CH:27]([CH3:28])[CH3:29])[CH2:26][CH:19]2[N:18]([S:39]([C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=2[Cl:49])(=[O:41])=[O:40])[CH2:17]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 86761388Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

Product 1

HCID 591342523-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dioneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

206 ml (1.44 mmol) of trimethylsilyl iodide (TMSI) are added to a solution of 250 mg (0.36 mmol) of benzyl[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate in 10 ml of CH3CN at 0° C. The reaction solution is allowed to reach room temperature and is stirred at this temperature for 2 h. 5 ml of MeOH are added to the reaction solution, and then the solution is concentrated in vacuo. The residue is purified on a 5 g SCX cartridge (eluted with MeOH followed by 3N NH3/MeOH). 185 mg of the desired compound are obtained as a white powder. LC/MS 558.07 (calculated, monoisotopic); measured value (M+H)+: 559.10

Workup

  1. customto reach room temperature
  2. concentrationthe solution is concentrated in vacuo
  3. customThe residue is purified on a 5 g SCX cartridge (eluted with MeOH followed by 3N NH3/MeOH)

Sources & evidence

ORD record
ord-a5e86eb6162f46c4bceea5d9d60fd624
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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