2-(Tributylstannyl)pyridine → 7-(1-azidoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1429791Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.[N:20]([CH:23]([C:25]1[N:26]=[C:27]2[S:35][CH:34]=[C:33]([CH3:36])[N:28]2[C:29](=[O:32])[C:30]=1Br)[CH3:24])=[N+:21]=[N-:22]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:20]([CH:23]([C:25]1[N:26]=[C:27]2[S:35][CH:34]=[C:33]([CH3:36])[N:28]2[C:29](=[O:32])[C:30]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:24])=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-(tributylstannyl)pyridine (Aldrich, 0.176 g, 0.382 mmol), 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (from example 8, step 3; 0.10 g, 0.318 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.0184 g, 0.0159 mmol) in 1,4-dioxane (0.5 mL) was heated at 65° C. overnight. After being cooled and quenched with saturated ammonium chloride, the resulting mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexane, to provide the desired product (13 mg, 13%). LCMS calculated for C14H13N6OS (M+H)+: m/z=313.1. Found: 313.0.

Workup

temperatureAfter being cooled
customquenched with saturated ammonium chloride
extractionthe resulting mixture was extracted with EtOAc
washwashed with brine
customdried
customevaporated to dryness
customThe residue was purified on silica gel
washeluting with 0 to 100% EtOAc in hexane

Sources & evidence

ORD record: ord-c6cdb77767f34487a2366043bfc1d67b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940752B2

Reaction notes

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