ethyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-phenylalaninate → 2-chloro-7-methyl-8-phenyl-7,8-dihydropteridin-6(5H)-one

HRID 530110Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:9]([C:11](OCC)=[O:12])[CH3:10])[C:5]([N+:22]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:22][C:11](=[O:12])[CH:9]([CH3:10])[N:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of ethyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-phenylalaninate (1.6 g, 4.56 mmol) in glacial acetic acid (35 mL) was added iron powder (1.6 g, 28.57 mmol). The resulting mixture was heated at 70° C. for 2 h. The insoluble material was then filtered off celite to give a clear solution. The bulk of solvent was evaporated to give a crude residue, which was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane) to afford desired product (75%). 1HNMR (300 MHz, DMSOd6): δ 1.29 (d, J=6.6 Hz, 3H), 4.58-4.60 (m, 1H), 7.36-7.50 (m, 5H), 7.70 (s, 1H) and 10.94 (s, 1H).

Workup

filtrationThe insoluble material was then filtered off celite
customto give a clear solution
customThe bulk of solvent was evaporated
customto give a crude residue, which
customwas purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane)

Sources & evidence

ORD record: ord-389da24227824e70b703616255fcd2c9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351974B2

Reaction notes

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