2-Amino-1-butanol, (+)- → 2-(s)-[2,5-Dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidin-4-ylamino]-butan-ol

HRID 967951Notes

Reaction equation

Cl[C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=[C:4]([CH3:19])[N:3]=1.[NH2:20][C@@H:21]([CH2:24][CH3:25])[CH2:22][OH:23]>CS(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]([CH3:8])=[C:6]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-chloro-2,5-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) δ 6.841 (s, 2H), 5.72 (brs, 1H), 4.45 (d, 1H), 3.82-3.95 (m, 1H), 3.71-3.9 (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

customThe mixture was quenched with water
extractionextracted with ethyl acetate
customThe organic layer was separated
customdried
concentrationconcentrated
customto give a crude material
customThe crude residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-e882c79489ac4575a6534ae3a848f3eb
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956047B1

Reaction notes

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