Water → Ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 81945Notes

Reaction equation

HRID 81945 reaction equation
CN([CH:4]=[C:5]1[C:13](=O)[C:12]2[N:11]([CH3:15])[N:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]=2[CH2:7][CH2:6]1)C.C(=O)(O)O.[NH2:25][C:26]([NH2:28])=[NH:27].O>CN(C=O)C>[NH2:27][C:26]1[N:28]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:10][N:11]([CH3:15])[C:12]=3[C:13]=2[N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 67075650ethyl 6-[(dimethylamino)methylene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

Product 1

HCID 57444093Ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateYield 164.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 16.62 g (60 mmol) of ethyl 6-[(dimethylamino)methylene]-7-oxo-1-methyl-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate in 0.5 L of DMF, 27 g (150 mmol) of guanidine carbonate was added. The mixture was stirred at 110° C. overnight. After cooling the mixture was poured into water (2.5 L) and stirred for 30 minutes. The precipitate was filtered, washed with water and dried to yield 26.83 g of title compound (91%).

Workup

  1. temperatureAfter cooling the mixture
  2. stirringstirred for 30 minutes
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-144ba9531d5744d5aa961aa3f4d7ebf8
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Reaction notes

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