Dimethyl Sulfoxide → 2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carbaldehyde

HRID 2110697Notes

Reaction equation

HRID 2110697 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[N:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[N:14]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][C:13]1[N:18]=[C:17]([CH:19]=[O:20])[CH:16]=[C:15]([NH:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[N:14]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57636124{2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol2×

Product 1

HCID 576360172-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carbaldehydeYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of oxalyl chloride (305 μL, 3.55 mmol) in DCM (10 mL) is chilled to −78° C. To the chilled solution is added dropwise, dimethyl sulfoxide (492 μL, 6.92 mmol). After 10 minutes of stirring a solution of {2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol [500 mg, 1.73 mmol, Intermediate (58)] in DCM (7 mL) is added via syringe. The mixture is stirred at −78° C. for 30 minutes before adding, triethylamine (1.95 mL, 13.84 mmol) via syringe. After stirring for an additional 40 minutes at −78° C. the reaction is poured into water (30 mL) and this mixture is extracted twice with 30 ml DCM. The combined extracts are dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The residue is taken up in toluene and re-concentrated and dried under high vacuum to afford 2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carbaldehyde [450 mg, 90.5%, Intermediate (59)].

Workup

  1. additionTo the chilled solution is added dropwise
  2. additionis added via syringe
  3. additionbefore adding
  4. stirringAfter stirring for an additional 40 minutes at −78° C. the reaction
  5. extractionthis mixture is extracted twice with 30 ml DCM
  6. dry with materialThe combined extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporator
  9. concentrationre-concentrated
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-dc4839d2435e4cee987f1c754cf5fbb9
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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