Ethyl imidazo[1,2-a]pyridine-6-carboxylate → 1-tert-butyl-6-pyridin-4-yl-3-(pyridin-4-ylmethyl)-2H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 487308Notes

Reaction equation

HRID 487308 reaction equation
C(C1C=CC2N(C=CN=2)C=1)(OCC)=O.[C:15]([N:19]1[C:23]([NH2:24])=[C:22]([C:25]([NH2:27])=[O:26])[C:21]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[N:20]1)([CH3:18])([CH3:17])[CH3:16].[CH:35]1([N:40]2[C:44](N)=[C:43](C(N)=O)[C:42]([CH2:49]C)=N2)[CH2:39]CCC1>>[C:15]([N:19]1[C:23]2=[N:24][C:49]([C:42]3[CH:39]=[CH:35][N:40]=[CH:44][CH:43]=3)=[N:27][C:25](=[O:26])[C:22]2=[C:21]([CH2:28][C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)[NH:20]1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 3

HCID 11830209Ethyl imidazo[1,2-a]pyridine-6-carboxylateHCID 194328401-tert-butyl-3-(4-pyridylmethyl)-5-amino-1H-pyrazole-4-carboxamideHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 1784487651-tert-butyl-6-pyridin-4-yl-3-(pyridin-4-ylmethyl)-2H-pyrazolo[3,4-d]pyrimidin-4-oneYield 84%

Procedure

Following a procedure substantially similar to that described in Example 16, part c, but substituting ethyl isonicotinate for 6-carboethoxyimidazo[1,2-a]pyridine and 1-tert-butyl-3-(4-pyridylmethyl)-5-amino-1H-pyrazole-4-carboxamide for 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide there was obtained 1-tert-butyl-3-(4-pyridylmethyl)-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one in 84% yield as a white powder, m.p. 233°-235° C.

Sources & evidence

ORD record
ord-df1378e2cfcf4f3cbaf8f63c366b4341
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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