Dimethylformamide → HCID 66824465, compound

HRID 1468612Notes

Reaction equation

HRID 1468612 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:15])[C:7](=[O:14])[N:8]2[CH2:11][CH2:12][OH:13])=[C:4]([NH:16][NH2:17])[N:3]=1.[CH:18]1[CH:19]=[CH:20]C2N(O)N=NC=2[CH:23]=1.CN1CC[O:32]CC1.CN(C)[CH:37]=[O:38]>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:15])[C:7](=[O:14])[N:8]2[CH2:11][CH2:12][OH:13])=[C:4]([NH:16][NH:17][C:23]([C:18]2[O:38][CH:37]=[CH:20][CH:19]=2)=[O:32])[N:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 66824634HCID 66824634, compound

Product 1

HCID 66824465HCID 66824465, compoundYield 84%

Conditions

Temperature
26 °C

Procedure

2-amino-6-hydrazino-9-(2-hydroxyethyl)-7-methyl-purin-8-one (4.5 g, 18.18 mmol) obtained in step 4,2-furoic acid (2.53 g, 22.5 mmol), HOBT (2.53 g, 18.8 mmol) and N-methylmorpholine were taken in dimethylformamide (40 ml). 1-Ethyl-3(3′-dimethylaminopropryl)carbodiimide hydrochloride (EDCI.HCl) (5.4 g, 28.2 mmol) was added to the reaction mixture and stirred at 25-27° C. for 14 hours. The reaction mixture was evaporated and residue was purified by column chromatography to obtain N′-[2-amino-9-(2-hydroxyethyl)-7-methyl-8-oxo-purin-6-yl]furan-2-carbohydrazide (5.3 g, 84%) as an off white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customresidue was purified by column chromatography

Sources & evidence

ORD record
ord-235d9a0d252a49bca9a4003a70dede86
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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