Trifluoroacetic acid → 3-(5-Isopropenyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 426276Notes

Reaction equation

[C:1]([C:4]1[C:5]([C:24]([C:26]2[CH:27]=[C:28]([CH:31]=[C:32]([CH3:34])[CH:33]=2)[C:29]#[N:30])=[O:25])=[N:6][C:7]([O:17]CC[Si](C)(C)C)=[N:8][C:9]=1[O:10]CC[Si](C)(C)C)([CH3:3])=[CH2:2].C(O)(C(F)(F)F)=O>ClCCl>[C:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:17])[NH:6][C:5]=1[C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([CH3:34])[CH:33]=1)[C:29]#[N:30])=[O:25])([CH3:3])=[CH2:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[5-isopropenyl-2,6-bis-(2-trimethylsilanyl-ethoxy)-pyrimidine-4-carbonyl]-5-methyl-benzonitrile (0.636 g, 1.28 mmol) in dichloromethane (10 mL) at 0° C. was added TFA (2 mL). Reaction mixture was stirred at 0° C. for 30 min, concentrated and purified by flash column chromatography (silica gel, 0 to 10% methanol/dichloromethane) to give a yellow solid (0.311 g, 82%). 1H NMR (300 MHz, CD3OD): δ 8.11 (s, 1H), 8.03 (s, 1H), 7.88 (s, 1H), 4.91 (s, 1H), 4.75 (s, 1H), 2.49 (s, 3H), 1.82 (s, 3H). Mass spectrum: 296.1 (M+H)+.

Workup

customReaction mixture
concentrationconcentrated
custompurified by flash column chromatography (silica gel, 0 to 10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-e83ce6df50ee425c812ad0c05dcb852f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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