Potassium Carbonate → HCID 54413738, compound

HRID 1003408Notes

Reaction equation

HRID 1003408 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8](Cl)[N:9]=2)[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].C(B(CC)[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:9]=2)[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 18796944HCID 18796944, compound

Product 1

HCID 54413738HCID 54413738, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of the methyl 7-amino-2-chloro-thieno[2,3-b]pyrazine-6carboxylate prepared as described in Example 10C (0.468 g), diethyl(3-pyridyl)borane (0.293 g), Pd(dppf)Cl2 (0.157 g), and K2CO3 (0.800 g) in degassed DMF (10 mL) was heated to 95° C. for 1.5 h, cooled, quenched in sat'd NH4Cl, the solid precipitate collected, washed with water and dried. Purification by silica gel column chromatographed provided 0.44 g (80%) of the title compound. 1H NMR (DMSO-d6) δ 3.87 (3H, s), 7.25 (2H, br s), 7.6 (1H, dd), 8.75 (2H, m), 9.49 (1H, s), 9.58 (1H, m).

Workup

  1. temperaturecooled
  2. customquenched in sat'd NH4Cl
  3. customthe solid precipitate collected
  4. washwashed with water
  5. customdried
  6. customPurification by silica gel column
  7. customchromatographed

Sources & evidence

ORD record
ord-ec3ad39364654ef1b35f413a0e4aa361
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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