Tyramine → HCID 69781830, compound

HRID 1355800Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](SC)[N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]O)=[O:25])[CH:19]=1.[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([NH:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:26][C:24](=[O:25])[C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[CH:19]=3)=[CH:33][CH:32]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirred suspension of 1.6 g (6.9 mmol) 2-amino-4-(2-furyl)-6-(methylthio)-5-pyrimidinecarbonitrile in 100 ml dichloromethane was added 3.6 g (20.7 mmol) m-chloroperbenzoic acid (70% purity) and stirring continued for 15 minutes at 0° C. The reaction mixture was then concentrated in vacuo and residue resuspended in 100 ml DME. To this stirred suspension were added 0.47 g (3.4 mmol) tyramine and 1.4 ml (10.3 mmol) DBU and the mixture heated at 100° C. for 1 hour. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether afforded 160 mg (5%) 3-chloro-benzoic acid 4-[2-(2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-ylamino)-ethyl]-phenyl ester as a white crystalline solid. ES-MS m/e (%): 484 (M{37Cl}+Na+, 10), 482 (M{35Cl}+Na+, 25), 462 (M{37Cl}+H+, 35), 460 (M{35Cl}+H+, 100).

Workup

stirringstirring
concentrationThe reaction mixture was then concentrated in vacuo and residue
temperaturethe mixture heated at 100° C. for 1 hour
concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-40279953bc214c0c8f7ee2eebb19e5b0
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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