Dimethyl Sulfoxide → 2-(s)-[2,5-Dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidin-4-ylamino]-butan-ol

HRID 1737670Notes

Reaction equation

HRID 1737670 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:19])[NH:5][C:6](C)([O:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[CH:7]=1.[NH2:20][C@@H:21]([CH2:24][CH3:25])[CH2:22][OH:23].[CH3:26]S(C)=O>>[CH3:19][C:4]1[N:3]=[C:2]([NH:20][C@@H:21]([CH2:24][CH3:25])[CH2:22][OH:23])[C:7]([CH3:26])=[C:6]([O:8][C:9]2[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=2[CH3:15])[N:5]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1200842-Amino-1-butanol, (+)-HCID 178432863HCID 178432863, compound

Product 1

HCID 183927812-(s)-[2,5-Dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidin-4-ylamino]-butan-ol

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-2,6-dimethyl-6-(2,4,6-trimethylphenyoxy)-pyrimidine (30 mg) and 2-(S)-amino-1-butanol (0.5 ml) in 0.5 ml of DMSO was heated at 130° C. for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a crude material. The crude residue was purified through silica gel column chromatography to give 24 mg of the title compound as white crystals. High MS for (C19H27N3O2) calc. 329.2103, found 329.21249; IR(KBr) 3400, 2940,1580 cm-1 ; 1H NMR (CDCl3) δ6.841 (s, 2H), 5.72 (brs, 1H), 4.45 (d, 1H), 3.82-3.96 (m, 1H), 3.72-3.9 (m, 1H), 3.5-3.6 (m, 1H), 2.27 (s, 3H), 2.21 (s, 3H), 2.08 (s, 3H), 2.02 (s, 6H), 1.4-1.7 (m, 2H), 1.03 (t, 3H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude material
  7. customThe crude residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-f3dff6d6f82643e9a3242342834d722e
Source dataset
uspto-grants-1999_10
Patent number
US05962479

Reaction notes

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