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

HRID 58244
Notes
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Reaction equation

HRID 58244 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 581114387-(1-azidoethyl)-6-bromo-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 866500667-(1-azidoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 13.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 31275
1,4-Dioxane
Solvent

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

  1. temperatureAfter being cooled
  2. customquenched with saturated ammonium chloride
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washwashed with brine
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-30587980d95b4287b0aaa8d0fe257e0e
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434746B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes