Diethyl Ether → 2-(Diethoxymethyl)pyrimidin-5-amine

HRID 1767747Notes

Reaction equation

HRID 1767747 reaction equation
[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[C:5]1[N:10]=[CH:9][C:8]([N:11]=CN(C)C)=[CH:7][N:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].CCOCC>O1CCOCC1>[CH2:17]([O:16][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[N:6]=[CH:7][C:8]([NH2:11])=[CH:9][N:10]=1)[CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 21114547HCID 21114547, compound

Product 1

HCID 211145462-(Diethoxymethyl)pyrimidin-5-amineYield 94.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Diethoxymethyl-5-(dimethylaminomethyleneamino)pyrimidine (6.3 g, 25 mmol) and a 5% aqueous solution of potassium carbonate (69 ml) in dioxane (40 ml) were heated at reflux for 6 hours. The reaction mixture was concentrated to a yellow solid which was triturated with ether to 2-diethoxymethyl-5-aminopyrimidine as a cream solid (4.64 g, 92% yield):

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated to a yellow solid which

Sources & evidence

ORD record
ord-3af21647ff864b2083ac2229c528e0e8
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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