2-Methoxyethanol → HCID 178496154, compound

HRID 1951294Notes

Reaction equation

HRID 1951294 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[NH2:6][C:7]1[CH:11]=[C:10](O)[NH:9][N:8]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:10]1[NH:9][N:8]=[C:7]([NH2:6])[CH:11]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 962215-Amino-1H-pyrazol-3-olHCID 4622928Cyanomethylenetributylphosphorane

Product 1

HCID 178496154HCID 178496154, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-methoxyethanol (0.664 mL, 8.41 mmol) and 3-amino-5-hydroxypyrazole (1.00 g, 10.1 mmol) in C6H6 (50 mL) at RT was added cyanomethylenetri-n-butylphosphorane (2.03 g, 8.41 mmol). The mixture was heated to 90° C. in a pressure vessel. After 16 hrs, the solvent was removed in vacuo. The residue was taken up in CH2Cl2 and adsorbed onto silica gel prior to purification by silica gel chromatography using 2-10% MeOH in CH2Cl2 with 1% NH4OH to afford 5-(2-methoxyethoxy)-1H-pyrazol-3-amine as a yellow oil. MH+=158.2.

Workup

  1. customthe solvent was removed in vacuo
  2. customto purification by silica gel chromatography

Sources & evidence

ORD record
ord-d104ebc6b4ca4e4babdb55d8f29d1b5d
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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