3-Amino-5-phenylpyrazole → HCID 178515642, compound

HRID 2172556Notes

Reaction equation

HRID 2172556 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH2:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](=O)[CH2:19][C:20](OC)=[O:21]>C(O)(=O)C>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]1[NH:12][C:10]2[N:9]([N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[C:20](=[O:21])[CH:19]=1

Participants

4

Reactant 2

HCID 1366553-Amino-5-phenylpyrazoleHCID 228584methyl 2-furoylacetate

Product 1

HCID 178515642HCID 178515642, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-phenyl-1H-pyrazol-5-amine (1: 0.318 g, 2.0 mmol, 1.0 eq) and methyl 3-(furan-2-yl)-3-oxopropanoate (0.370 g, 2.2 mmol, 1.10 eq) was heated in acetic acid (2.0 mL) at 100° C. for 4 hr. After cooling down to rt, the precipitate was collected by filtration. The precipitate was rinsed with EtOH (15 mL) and dried under air to afford 5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one (0.358 g, 65%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 12.70 (s, 1H), 8.06 (m, 1H), 8.00 (m, 1H), 7.98 (m, 1H), 7.51-7.47 (m, 3H), 7.44-7.42 (m, 1H), 6.81 (dd, J=3.7, 1.8 Hz, 1H), 6.64 (s, 1H), 6.15 (s, 1H).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washThe precipitate was rinsed with EtOH (15 mL)
  3. customdried under air

Sources & evidence

ORD record
ord-760fb89b022c42088b2f7795a3e40ac0
Source dataset
uspto-grants-2015_06
Patent number
US09056111B1

Reaction notes

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