Tetrahydrofuran → Ethyl 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine-1-acetate

HRID 400392Notes

Reaction equation

HRID 400392 reaction equation
C1COCC1.[Cl:6][C:7]1[N:12]=[C:11](Cl)[C:10]([CH:14]=O)=[C:9]([Cl:16])[N:8]=1.Cl.[NH:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH2:19]>C(N(CC)CC)C>[Cl:16][C:9]1[N:8]=[C:7]([Cl:6])[N:12]=[C:11]2[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=[CH:14][C:10]=12

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehydeHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 86069460Ethyl 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine-1-acetateYield 44.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

155 ml of THF are added with stirring to a mixture of 5.17 g of 2,4,6-tri-chloropyrimidine-5-carbaldehyde and 5.85 g of ethyl hydrazinoacetate hydrochloride. The mixture is cooled to 10° C., and 6.78 ml of triethylamine are added dropwise. The mixture is stirred at RT for a further 1 h. The deposited precipitate is separated off (not the product). The filtrate, which contains the product, is subjected to conventional work-up, giving 3 g of ethyl (4,6-dichloropyrazolo[3,4-d]pyrimidin-1-yl)acetate (“12”).

Workup

  1. customThe deposited precipitate is separated off (not the product)

Sources & evidence

ORD record
ord-2d090c3dd12842119556597e95e96285
Source dataset
uspto-grants-2014_06
Patent number
US08741896B2

Reaction notes

Loading…