Diisopropylethylamine → 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1737619Notes

Reaction equation

HRID 1737619 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][NH:16][CH3:17])[N:9]=[CH:8][N:7]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]2=[O:26].ClC1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=1.[CH:35](N(CC)C(C)C)(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]([CH3:35])[C:17]1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=1)[N:9]=[CH:8][N:7]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])[C:6]2=[O:26]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 5817964-Chloro-6-methylpyrimidineHCID 226249706-Methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 226250876-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 80%

Procedure

A solution of 6-methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (363 mg, 1 mmol) and 4-chloro-6-methylpyrimidine (257 mg, 2 mmol), (J. Het. Chem., 1969, 6, 879), in N,N-diisopropylethylamine (2 ml) was heated at reflux for 30 minutes. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (365 mg, 80%).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-dd74c9308524419a9fb2df2307cd8abf
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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