3,4,5-Trimethoxyaniline → HCID 21995314, compound

HRID 1977686Notes

Reaction equation

HRID 1977686 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[NH2:23]>>[O:11]([C:9]1[CH:8]=[CH:7][N:6]=[C:5]([NH:23][C:22]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:20]([O:19][CH3:18])[CH:21]=2)[N:10]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 15405455HCID 15405455, compound

Product 1

HCID 21995314HCID 21995314, compoundYield 1.7%

Procedure

2-Methylsulphonyl-4-phenoxypyrimidine (0.76 g, 3.04 mmol) and 3,4,5-trimethoxyaniline (0.56 g, 4.0 mmol) were heated as a melt at 140° for 2 h. On cooling the residue was partitioned between ethyl acetate (50 ml) and 2M hydrochloric acid (50 ml), and the organic layer was washed with water (50 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to column chromatography [silica 20% ethyl acetate-hexane] to give the title compound (18 mg) as a white solid m.p. 149° after recrystallisation from ethyl acetate. δH (CDCl3) 8.26 (1H, d, J 5.6 Hz), 7.39 (2H, m), 7.26 (1H,m), 7.18-7.15 (2H, m), 6.73 (2H, s), 6.31 (1H, d, J 5.6 Hz), 3.77 (3H, s) and 3.64 (6H, s). MS m/z 354 (M+H)+.

Workup

  1. temperatureOn cooling the residue
  2. customwas partitioned between ethyl acetate (50 ml) and 2M hydrochloric acid (50 ml)
  3. washthe organic layer was washed with water (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a6f3c3b7b804ac0b16e85457d977281
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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