Formamide → 1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(3aH)-one

HRID 1518310Notes

Reaction equation

HRID 1518310 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=O.[CH:20]([NH2:22])=O>>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:2]3=[N:1][CH:20]=[N:22][C:15](=[O:17])[CH:3]3[CH:4]=[N:5]2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 4456866Ethyl 5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 594475481-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(3aH)-one

Conditions

Temperature
180 °C

Procedure

A mixture of compound 44A (7 g, 26.8 mmol) and formamide (64.1 mL, 1607 mmol) was heated at 180° C. overnight and cooled. The precipitate was collected, washed with water and dried to provide the desired product: 1H NMR (400 MHz, DMSO-D6) δ ppm 12.35 (1H, s), 8.28 (1H, s), 8.15 (1H, s), 7.85-7.93 (2H, m), 7.09-7.14 (2H, m), 3.82 (3H, s).

Workup

  1. temperaturecooled
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3dadf241305c4604a67cfb31f9b36dc4
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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