Potassium Carbonate → HCID 178494122, compound

HRID 474558Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](=[NH:13])[NH2:12])[CH:5]=[CH:6][C:7]=1[F:8].[OH:14]/[CH:15]=[C:16](/[CH2:21][C:22]1[CH:23]=[N:24][C:25]([O:28][CH3:29])=[N:26][CH:27]=1)\[C:17](OC)=O.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH2:9][CH2:10][C:11]1[NH:12][CH:17]=[C:16]([CH2:21][C:22]2[CH:23]=[N:24][C:25]([O:28][CH3:29])=[N:26][CH:27]=2)[C:15](=[O:14])[N:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The mixture of 3-(3-bromo-4-fluorophenyl)propanimidamide (3.28 g, 13.38 mmol), methyl (2Z)-3-hydroxy-2-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-propenoate (1.5 g, 6.69 mmol) and K2CO3 (2.77 g, 20.07 mmol) in NMP (20 mL) was heated with a microwave reactor at 130° C. for 2 h. The mixture was purified with a reverse phase Biotage to provide the title compound (1.2 g, 40.6% yield). LCMS: rt=2.52 min, [M+H+]=419

Workup

customThe mixture was purified with a reverse phase Biotage

Sources & evidence

ORD record: ord-90c89de6ab1a484f941d22a1f286063b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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