2,2,6-Trimethyl-4H-1,3-dioxin-4-one → HCID 69733596, compound

HRID 2416414Notes

Reaction equation

[C:1]([O:4][C@H:5]([CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[C:13]([NH2:17])[N:12]([CH3:18])[C:11]1=[O:19])(=[O:3])[CH3:2].CC1(C)[O:27][C:26](=O)[CH:25]=[C:24]([CH3:29])O1>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:1]([O:4][C@H:5]([CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:26](=[O:27])[CH:25]=[C:24]([CH3:29])[NH:17][C:13]=2[N:12]([CH3:18])[C:11]1=[O:19])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

Alternatively, (R)-3-(5-acetoxyhexyl)-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione was prepared as follows: To a mixture of (R)-3-(5-acetoxyhexyl)-6-amino-1-methyluracil (2.1 g, 7.41 mmol) in xylenes (70 ml) heated to 160° C. was added over 30 minutes a solution of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (2.0 ml, 15.3 mmol) in xylenes (30 ml). After stirring at 160° C. for 20 minutes, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-toluene to afford(R)-3-(5-acetoxyhexyl)-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.37 g, 53% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (d, 3H), 1.25-1.71 (m, 6H), 2.00 (s, 3H), 2.46 (s, 3H), 3.62 (s, 3H), 4.00 (t, 2H), 4.86 (sextet, 1H), 6.49 (s, 1H), 12.15 (s, 1H).13C NMR (75 MHz, CDCl3) δ 19.64, 20.96, 22.46, 25.02, 27.19, 29.15, 35.19, 40.67, 70.29, 94.48, 105.71, 150.09, 150.73, 164.92, 165.18, 167.82, 170.15.

Workup

temperaturethe mixture was cooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-27addbb2ca9244fca4482203f4061059
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825180B2

Reaction notes

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