2-Isocyanatoethyl methacrylate → HCID 178454713, compound

HRID 215696

Reaction equation

[CH3:1][C:2]1[NH:8][C:7]([NH2:9])=[N:6][C:4](=[O:5])[CH:3]=1.[C:10]([O:15][CH2:16][CH2:17][N:18]=[C:19]=[O:20])(=[O:14])[C:11]([CH3:13])=C.[CH2:21]([Sn](=O)CCCC)CCC>CC(N(C)C)=O>[CH3:1][C:2]1[NH:8][C:7]([NH:9][C:19]([NH:18][CH2:17][CH2:16][O:15][C:10](=[O:14])[CH:11]=[CH:13][CH3:21])=[O:20])=[N:6][C:4](=[O:5])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

37.5 g (0.3 mol) 6-methylisocytosine, 55.8 g (0.36 mol) 2-isocyanatoethyl methacrylate and 3.7 g (0.015 mmol) dibutyltin oxide were added to 400 ml dimethylacetamide. 100 mg BHT was added and the mixture was heated to 90° C. for one hour. The mixture was filtered at 90° C. Upon cooling down to room temperature 2-methyl-2-propenoic acid-2-[[[(1,4-dihydro-6-methyl-4-oxo-2-pyrimidinyl)amino]carbonyl]amino]ethyl ester started to crystallize. The mixture was stirred for two and a half hour. 500 ml acetone was added and 3-methyl-2-propenoic acid-2-[[[(1,4-dihydro-6-methyl-4-oxo-2-pyrimidinyl)amino]carbonyl]amino]ethyl ester was isolated by filtration. 2-methyl-2-propenoic acid-2-[[[(1,4-dihydro-6-methyl-4-oxo-2-pyrimidinyl)amino]carbonyl]amino]ethyl ester was treated with 500 ml acetone, again isolated by filtration and dried. 68.6 g (82%) of 2-methyl-2-propenoic acid-2-[[[(1,4-dihydro-6-methyl-4-oxo-2-pyrimidinyl)amino]carbonyl]amino]ethyl ester was isolated (m.p.:208° C.).

Workup

addition100 mg BHT was added
filtrationThe mixture was filtered at 90° C
temperatureUpon cooling down to room temperature 2-methyl-2-propenoic acid-2-[[[(1,4-dihydro-6-methyl-4-oxo-2-pyrimidinyl)amino]carbonyl]amino]ethyl ester
customto crystallize
addition500 ml acetone was added

Sources & evidence

ORD record: ord-927182cec925424f8410152396a87b1f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08192918B2

Linked notes

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