Sodium → HCID 178448295, compound

HRID 415356Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:17]CC3C=CC=CC=3)=[N:6][C:5]=2[N:25]=1.[Na]>N>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:17])=[N:6][C:5]=2[N:25]=1

Participants

Conditions

Temperature: -33 °C

Procedure

A round-bottomed flask was equipped with a dry ice-ethanol condenser and immersed in a dry ice-ethanol cooling bath. Ammonia (250 mL) was condensed into the flask followed by addition of (2R)-2-{[2-amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino}pentan-1-ol (6.8 g, 18.1 mmol). The resulting mixture was allowed to warm to −33° C. and sodium metal was added in small pieces until a blue colour appeared and persisted for 30 seconds. The reaction was then quenched by addition of a spoonful of solid ammonium chloride. The ammonia was evaporated off and water (250 mL) was added to the residue. The resulting mixture was neutralized with 1M HCl (aq). The precipitated product was collected by filtration, washed with water and dried in vacuo to yield 4.15 g (80% yield) of the title compound.

Workup

customA round-bottomed flask was equipped with a dry ice-ethanol condenser
customimmersed in a dry ice-ethanol cooling bath
customcondensed into the flask
customThe reaction was then quenched by addition of a spoonful of solid ammonium chloride
customThe ammonia was evaporated off
additionwater (250 mL) was added to the residue
filtrationThe precipitated product was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-483978856ff04205b459f67a12eb5257
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088780B2

Reaction notes

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