Water → 1-(4,6-Di(pyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

HRID 447068Notes

Reaction equation

HRID 447068 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=[C:4](Br)[N:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1)CCC.O>CN(C=O)C.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:24]1[CH:25]=[CH:26][N:27]=[CH:28][C:23]=1[C:2]1[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=[C:4]([C:28]2[CH:23]=[N:24][CH:25]=[CH:26][N:27]=2)[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 27373162-(Tributylstannyl)pyrazineHCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

Product 1

HCID 426331061-(4,6-Di(pyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)-3-ethylureaYield 7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1-(4,6-dibromo-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-urea (0.06 g, 0.16 mmol) in DMF (3 mL) was added 2-(tributylstannyl)pyrazine (0.10 mL, 0.32 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was degassed by bubbling nitrogen for 10-15 min followed by addition of Pd(PPh3)4 (0.018 g, 0.015 mmol). The resulting solution was again degassed for 15-20 min followed by heating up to 95° C. overnight. After completion of reaction (TLC monitoring), the reaction mixture was cooled, added water (30 mL) and extracted with ethyl acetate (3×20 mL). The combined organics was dried over Na2SO4 and evaporated to dryness under high vacuum. The crude residue was purified over silica-gel (100-200 M, 2% MeOH-DCM) to get the desired product (0.004 g, 7%).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen for 10-15 min
  3. customThe resulting solution was again degassed for 15-20 min
  4. customAfter completion of reaction (TLC monitoring)
  5. temperaturethe reaction mixture was cooled
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialThe combined organics was dried over Na2SO4
  8. customevaporated to dryness under high vacuum
  9. customThe crude residue was purified over silica-gel (100-200 M, 2% MeOH-DCM)

Sources & evidence

ORD record
ord-a76cc259b54e492bb2891b62409a7e32
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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