Dimethyl Sulfoxide → 4-Ethoxy-2-methylamino-quinazoline-6-carbaldehyde

HRID 1783634Notes

Reaction equation

HRID 1783634 reaction equation
C(#N)C.CS(C)=O.[CH:8]([O-:10])=O.[Na+].Br[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][CH3:24])[N:17]=[C:16]2[O:25][CH2:26][CH3:27]>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.O>[CH2:26]([O:25][C:16]1[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([CH:8]=[O:10])[CH:14]=2)[N:19]=[C:18]([NH:23][CH3:24])[N:17]=1)[CH3:27]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6342AcetonitrileHCID 2723810Sodium FormateHCID 57590621(6-Bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine

Product 1

HCID 575906254-Ethoxy-2-methylamino-quinazoline-6-carbaldehydeYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a combined solution of acetonitrile (40 mL) and DMSO (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.65 g, 1.43 mmol), anhydrous sodium formate (5.82 g, 85.6 mmol) followed by powder (6-bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine (4 g, 14.3 mmol) and the resultant mixture was heated to 85° C., 50 psi under CO atmosphere. After being stirred for 48 hours, the cooled mixture was poured to water and extracted with DCM (3×200 mL). The combined organic phase was washed with brine, dried over Na2SO4, evaporated to give a brown solid which was purified by column to afford 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (1 g, 4.3 mmol, 30%) as a pale solid. 1H NMR (DMSO-d6): δ 9.95 (s, 1H), 8.38 (s, 1H), 8.00-7.97 (d, 1H), 7.59-7.56 (m, 1H), 7.46-7.44 (d, 1H), 4.53-4.48 (q, 2H), 2.89-2.87 (d, 3H), 1.44-1.40 (t, 3H).

Workup

  1. extractionextracted with DCM (3×200 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give a brown solid which
  6. customwas purified by column

Sources & evidence

ORD record
ord-d50480a27e734a2ca3c9743866018e63
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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