1,2-Dichloroethane → 3-(3,4-Dimethoxyphenyl)propynoic acid (6-amino-1-ethyl-3-prop-2-ynyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)amide

HRID 1666222Notes

Reaction equation

HRID 1666222 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH2:12][C:13]#[CH:14])[C:5](=[O:11])[N:6]([CH2:9][CH3:10])[C:7]=1[NH2:8].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:26]#[C:27][C:28](O)=[O:29])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].C(Cl)CCl.Cl.CN(C)CCCN=C=NCC>CO>[NH2:8][C:7]1[N:6]([CH2:9][CH3:10])[C:5](=[O:11])[N:4]([CH2:12][C:13]#[CH:14])[C:3](=[O:15])[C:2]=1[NH:1][C:28](=[O:29])[C:27]#[C:26][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37083353-(3,4-dimethoxyphenyl)prop-2-ynoic AcidHCID 598036905,6-Diamino-1-ethyl-3-propargyluracil

Product 1

HCID 598036863-(3,4-Dimethoxyphenyl)propynoic acid (6-amino-1-ethyl-3-prop-2-ynyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the 5,6-diamino-1-ethyl-3-propargyluracil (4.2 g, 20 mmol), 3,4-dimethoxyphenylacetylencarboxylic acid (4.2 g, 20 mmol) and EDC ((1-(3-dimethylaminopropyl)-3-ethyl-carbodiimid hydrochloride; 4.2 g, 22 mmol) in methanol (100 ml) was stirred at room temperature for 2 h. The colorless product was precipitated by adding water (ca. 150 ml), filtered under reduced pressure, washed thoroughly with ether (TLC-control indicated the purity of the product; eluent: dichloromethane/methanol 9:1) and dried at 60° C. Yield: 6 g (76%).

Workup

  1. customThe colorless product was precipitated
  2. additionby adding water (ca. 150 ml)
  3. filtrationfiltered under reduced pressure
  4. washwashed thoroughly with ether (TLC-control
  5. dry with materialeluent: dichloromethane/methanol 9:1) and dried at 60° C

Sources & evidence

ORD record
ord-d09b72cda67541beb1b1f7266f3f5bbe
Source dataset
uspto-grants-2011_10
Patent number
US08044061B2

Reaction notes

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