HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Diisopropylethylamine → HCID 57542080, compound

HRID 2353313
Notes
Print preview

Reaction equation

HRID 2353313 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([Cl:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1.[CH3:24][O:25][CH:26]([O:29][CH3:30])[CH2:27][NH2:28].C(N(C(C)C)CC)(C)C>O1CCOCC1>[Cl:13][C:6]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([NH:28][CH2:27][CH:26]([O:29][CH3:30])[O:25][CH3:24])[N:3]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 50878583Methyl [4,6-dichloro-2-(4-nitrobenzyl)pyrimidin-5-YL]acetate

Product 1

HCID 57542080HCID 57542080, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl [4,6-dichloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.0 g, 5.6 mmol), aminoacetaldehyde dimethylacetal (0.68 g, 6.5 mmol) and diisopropylethylamine (1.5 mL, 8.4 mmol) in 1,4-dioxane (50 mL) was stirred at 80° C. for 2 hours. The mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extracts were washed with aq NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative MPLC (silica gel, hexane:ethyl acetate, 2/1) to give methyl [4-chloro-6-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]-acetate (1.89 g, 79%) as a gray solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extracts were washed with aq NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative MPLC (silica gel, hexane:ethyl acetate, 2/1)

Sources & evidence

ORD record
ord-3775dc909ca84d329a5e3f8bc508db80
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07750014B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes