1,2-Dimethoxyethane → HCID 68750600, compound

HRID 1851314Notes

Reaction equation

HRID 1851314 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[C:15]([S:17][CH3:18])[N:16]=[C:4]2[N:3]=1.[OH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>O.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]>[CH3:18][S:17][C:15]1[N:16]=[C:4]2[N:3]=[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH2:20][OH:19])=[CH:22][CH:23]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 86703061HCID 86703061, compound2×

Product 1

HCID 68750600HCID 68750600, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-methylsulfanyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine (310 mg, 1.12 mmol), [4-(hydroxymethyl)phenyl]boronic acid (187 mg, 1.23 mmol), 2.32 mL Na2CO3 solution (10%), 56 mg 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) and 3.6 mL DME was heated at 100° C. for 50 min under microwave irradiation. In parallel, a second reaction was performed with a 100 mg portion of 5-chloro-2-methylsulfanyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine. On cooling, both mixtures were combined, diluted with water and extracted with CH2Cl2. The combined organic extract was washed with brine, dried and concentrated in vacuo to give the crude title compound which was used without further purification in the next step.

Workup

  1. customIn parallel, a second reaction
  2. temperatureOn cooling
  3. extractionextracted with CH2Cl2
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-283e3c067c094299a5db19ff8e5072b4
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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