[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]=1To 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.
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