Triethylamine → HCID 57613446, compound

HRID 912547Notes

Reaction equation

HRID 912547 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][S:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([C:14]2[C:15](O)=[N:16][CH:17]=[N:18][CH:19]=2)[CH:9]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:3][C:15]1[C:14]([C:10]2[CH:9]=[C:8]([S:7][CH3:6])[N:13]=[CH:12][N:11]=2)=[CH:19][N:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178503087HCID 178503087, compound

Product 1

HCID 57613446HCID 57613446, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

POCl3 (1.51 mL, 16.2 mmol, 3.0 eq.) is added slowly to a suspension of 6-methylsulfanyl-[4,5′]bipyrimidinyl-4′-ol 6 (1.20 g, 5.44 mmol) and triethyl amine (0.76 mL, 5.44 mmol, 1.0 eq.) in acetonitrile (30 ml). After heating at 85° C. for 2 hours, the reaction mixture is cooled to room temperature, poured into ice-water, neutralized by saturated NaHCO3 solution, and then extracted with ethyl acetate. The organic layer is washed with brine and dried over Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 40% to give 4′-chloro-6-methylsulfanyl-[4,5′]bipyrimidinyl as a white solid. 1H NMR 400 MHz (DMSO-d6) δ 9.19 (s, 1H), 9.12 (d, 1H, J=1.2 Hz), 9.07 (s, 1H), 7.91 (d, 1H, J=1.6 Hz), 2.62 (s, 3H).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel flash chromatography
  8. washeluting with ethyl acetate in hexanes from 0% to 40%

Sources & evidence

ORD record
ord-3dfdc154fb9c40c496c2749cd1f4cb4d
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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