5-(Tributylstannyl)-1,3-thiazole → HCID 57825995, compound

HRID 1689939Notes

Reaction equation

HRID 1689939 reaction equation
Br[C:2]1[C:3]2[S:17][CH:16]=[CH:15][C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[N:7]=1.C([Sn](CCCC)(CCCC)[C:23]1[S:27][CH:26]=[N:25][CH:24]=1)CCC>CC(N(C)C)=O.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>[S:27]1[C:23]([C:2]2[C:3]3[S:17][CH:16]=[CH:15][C:4]=3[N:5]=[C:6]([C:8]3[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=3)[N:7]=2)=[CH:24][N:25]=[CH:26]1

Participants

5

Reactant 2

HCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 42604469HCID 42604469, compound

Product 1

HCID 57825995HCID 57825995, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 3-(4-bromo-thieno[3,2-d]pyrimidin-2-yl)-phenol (150 mg, 0.49 mmol), 5-tributylstannanyl-thiazole (275 mg, 0.735 mmol), and Pd(PPh3)4 (28 mg, 0.0245 mmol) in anhydrous DMA (4 ml) was heated in a microwave at 150° C. for 15 mins. The reaction was extracted into ethyl acetate, washing with brine and water before drying the organic layer over MgSO4. The crude material was purified by flash column chromatography using 1:1 ethyl acetate/petrol as the eluent. The resulting solid was triturated with dichloromethane to give the title compound as an off-white solid (22 mg, 14%).

Workup

  1. extractionThe reaction was extracted into ethyl acetate
  2. washwashing with brine and water
  3. dry with materialbefore drying the organic layer over MgSO4
  4. customThe crude material was purified by flash column chromatography
  5. customThe resulting solid was triturated with dichloromethane

Sources & evidence

ORD record
ord-adcd0d367caf4498bcc9d5f749383a77
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

Loading…