Sodium Bicarbonate → HCID 59448347, compound

HRID 1925018Notes

Reaction equation

HRID 1925018 reaction equation
I[C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.C(=O)(O)[O-].[Na+].[CH3:14][O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[C:19](B(O)O)=[CH:18][N:17]=1>COCCOC.C(Cl)Cl.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>[CH3:7][C:5]1[N:6]=[C:2]([C:19]2[C:20]([O:22][CH3:23])=[N:21][C:16]([O:15][CH3:14])=[N:17][CH:18]=2)[S:3][C:4]=1[CH3:8]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 2110023329947-25-9

Product 1

HCID 59448347HCID 59448347, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-iodo-4,5-dimethyl-1,3-thiazole (prepared in a similar manner to that described in JACS 123 (6), 1017-1022, (2001), 250 mg, 1.046 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (4.357 ml). Tetrakis(triphenylphosphine)palladium(0) (60.4 mg, 0.052 mmol) was added and the mixture was stirred at room temperature for 10 minutes. Sodium bicarbonate (4.183 ml, 4.18 mmol) and [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (385 mg, 2.091 mmol) were added and the resulting mixture was stirred at 85° C. for 2 hours. The mixture was allowed to cool to rt and left standing at rt over the week end. The mixture was diluted with DCM (5 mL), the aqueous phases was separated and extracted with DCM (2×5 mL). The organics were combined and dried over sodium sulphate to give a yellow solid that was purified by silica chromatography, eluting with DCM:MeOH from 100:0 to 95:5 to afford the title compound as a pale yellow solid (143 mg).

Workup

  1. stirringthe resulting mixture was stirred at 85° C. for 2 hours
  2. temperatureto cool to rt
  3. waitleft
  4. customstanding at rt over the week end
  5. customthe aqueous phases was separated
  6. extractionextracted with DCM (2×5 mL)
  7. dry with materialdried over sodium sulphate
  8. customto give a yellow solid
  9. customthat was purified by silica chromatography
  10. washeluting with DCM

Sources & evidence

ORD record
ord-7b2255fee9774429be927dc20c9c5c6f
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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