Formamide → 1-(2-Hydroxy-2-phenylethyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 732934Notes

Reaction equation

HRID 732934 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([OH:18])=O.[CH:19]([NH2:21])=O>O>[OH:15][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][N:6]1[C:2]2[N:1]=[CH:19][NH:21][C:16](=[O:18])[C:3]=2[CH:4]=[N:5]1

Participants

4

Reactant 2

HCID 713FormamideHCID 108794365-amino-1-(2-hydroxy-2-phenylethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 1363835291-(2-Hydroxy-2-phenylethyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A suspension of 5 (2.75 g, 10 mmol) in formamide (10 g, 333 mmol) was heated at 190° C. for 8 h and then poured in H2O (300 mL). The crude was filtered and purified by dissolving in 2M NaOH (100 mL), boiling with coal, followed by precipitation with glacial acetic acid. The solid was filtered and recrystallized from absolute ethanol to give 10 (1.79 g, 70%) as a white solid: mp 270-271° C. 1H NMR: δ 4.25-4.55 (m, 2H, CH2), 5.05-5.15 (m, 1H, CHO), 5.65 (d, 1H, OH, disappears with D2O), 7.25-7.45 (m, 5H Ar), 8.05 (s, 1H, H-3), 8.10 (s, 1H, H-6), 12.15 (br s, 1H, NH, disappears with D2O). IR cm−1: 3400 (NH), 3245-2500 (OH), 1740 (CO). Anal. (C13H12N4O2) C, H, N.

Workup

  1. filtrationThe crude was filtered
  2. custompurified
  3. dissolutionby dissolving in 2M NaOH (100 mL)
  4. customfollowed by precipitation with glacial acetic acid
  5. filtrationThe solid was filtered
  6. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-86dba6ebcb86496495c52b03710c2216
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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