Water → HCID 136069591, compound

HRID 2278507Notes

Reaction equation

HRID 2278507 reaction equation
[Cl:1]N1C(=O)CCC1=O.[N:9]1([C:15]2[N:16]=[C:17]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH:18][C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.O.ClCCl>C(Cl)(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:17]1[NH:18][C:19](=[O:21])[C:20]([Cl:1])=[C:15]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:16]=1)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 135905419Ethyl 2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Product 1

HCID 136069591HCID 136069591, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.87 g of N-chlorosuccinimide are added to a solution of 3.75 g of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate described in example 6a (step (2′a)a) in 50 ml of chloroform. The reaction medium is stirred at ambient temperature for 2 hours. 20 ml of water and 50 ml of dichloromethane are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica column, eluent: 99/01 then 98/02 then 97/03 dichloromethane/methanol, so as to give 2.81 g of (5-chloro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetic acid ethyl ester, the characteristics of which are the following:

Workup

  1. dry with materialthe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified on a silica column, eluent

Sources & evidence

ORD record
ord-e5d3ff65d0564f3da7939164b876fa65
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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