Formamide → 1-isopropyl-3-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

HRID 530971Notes

Reaction equation

HRID 530971 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:3]=1[C:19]([NH2:21])=[O:20].[CH:22](N)=O>>[CH:7]([N:6]1[C:2]2[N:1]=[CH:22][NH:21][C:19](=[O:20])[C:3]=2[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[N:5]1)([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 713FormamideHCID 895866375-amino-1-isopropyl-3-(3-nitrophenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1364454491-isopropyl-3-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-oneYield 91%

Conditions

Temperature
160 °C

Procedure

Compound 27 (1 g, 3.46 mmol) was added to formamide (1.167 mL, 29.3 mmol) and heated to 160° C. for 40 hours. Afterwards, the reaction mixture was allowed to cool to room temperature and diluted into ice cold water. The mixture was filtered and a solid was collected (943 mg, 91% yield): 1H NMR (400 MHz, DMSO) δ 12.37 (s, 1H), 9.32 (s, 1H), 8.81 (d, J=7.8, 1H), 8.23 (d, J=8.1, 1H), 8.13 (s, 1H), 7.75 (t, J=8.0, 1H), 5.06 (hept, J=6.6, 1H), 1.52 (d, J=6.7, 6H); 13C NMR (100 MHz, DMSO) δ 157.77, 152.48, 148.16, 148.06, 143.85, 133.58, 129.95, 123.05, 122.07, 103.02, 49.07, 21.74; [M+H]+ calculated for C14H13N5O3 300.1, found 300.0.

Workup

  1. temperatureto cool to room temperature
  2. additiondiluted into ice cold water
  3. filtrationThe mixture was filtered
  4. customa solid was collected (943 mg, 91% yield)

Sources & evidence

ORD record
ord-747101d2dc264a41a9968fabdf271ee1
Source dataset
uspto-grants-2016_05
Patent number
US09353116B2

Reaction notes

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