Sodium → HCID 178448295, compound
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]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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 the 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 spoon 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 spoon 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-5d490bd26f6b43bea3b80eff36119ed8
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947693B2
Reaction notes
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