Water → HCID 178446222, compound

HRID 1097685Notes

Reaction equation

[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])[C:6](=[O:18])[N:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[N:3]=1.[OH2:24].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:32]O>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[NH:32])[NH:17][OH:24])[C:6](=[O:18])[N:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanenitrile (3.0 g, 8.9 mmol) in EtOH (30 ml) was treated with water (15 ml), potassium carbonate (1.48 g, 10.7 mmol) and hydroxylamine hydrochloride (0.74 g, 10.7 mmol) and then heated at 70° C. overnight. A further potassium carbonate (1.5 g, 10.9 mmol) and hydroxylamine hydrochloride (1.0 g, 14.5 mmol) were cautiously added to the mixture which was then heated to 90° C. for 24 h. The mixture was cooled and concentrated in vacuo to remove most of the EtOH. The residual mixture was treated with water (30 ml) and acidified to pH 7 by the cautious addition of 2M aqueous hydrochloric acid. The precipitated solid was filtered off, washed with water, then with diethyl ether and thoroughly dried to yield the title compound as a white solid (2.80 g, 85%).

Workup

temperaturewas then heated to 90° C. for 24 h
temperatureThe mixture was cooled
concentrationconcentrated in vacuo
customto remove most of the EtOH
additionThe residual mixture was treated with water (30 ml)
additionacidified to pH 7 by the cautious addition of 2M aqueous hydrochloric acid
filtrationThe precipitated solid was filtered off
washwashed with water
dry with materialwith diethyl ether and thoroughly dried

Sources & evidence

ORD record: ord-34d3b23842a8454bafc37bc66d96be3f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Reaction notes

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