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4-(Tri-n-butylstannyl)thiazole → 7-(1-azidoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58259
Notes
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Reaction equation

HRID 58259 reaction equation
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:16][CH:15]=[C:14]([CH3:17])[N:9]2[C:10](=[O:13])[C:11]=1Br)[CH3:5])=[N+:2]=[N-:3].C([Sn](CCCC)(CCCC)[C:23]1[N:24]=[CH:25][S:26][CH:27]=1)CCC>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:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:16][CH:15]=[C:14]([CH3:17])[N:9]2[C:10](=[O:13])[C:11]=1[C:23]1[N:24]=[CH:25][S:26][CH:27]=1)[CH3:5])=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 581114387-(1-azidoethyl)-6-bromo-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 866500697-(1-azidoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 81%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a mixture of 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.10 g, 0.32 mmol) and 4-(tributylstannyl)-1,3-thiazole (143 mg, 0.382 mmol) in 1,4-dioxane (3 mL) was added tetrakis(triphenylphosphine)palladium(0) (18.4 mg, 0.0159 mmol). The reaction mixture was heated at 120° C. overnight. After cooling to room temperature, the mixture concentrated under reduced pressure. The crude mixture was purified on silica gel, eluting with 0 to 60% EtOAc in hexane, to give the desired product (82 mg, 81%). LCMS calculated for C12H11N6OS2(M+H)+: m/z=319.0. Found: 319.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture concentrated under reduced pressure
  3. customThe crude mixture was purified on silica gel
  4. washeluting with 0 to 60% EtOAc in hexane

Sources & evidence

ORD record
ord-fe09c55721a64defbb37b930ab6972d2
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