methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate → (7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one

HRID 2364765Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:16]([CH3:18])[CH3:17])[C@@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:19]([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:19][C:10](=[O:11])[C@H:9]([CH2:14][CH3:15])[N:8]([CH:16]([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 43b (8.74 g, 27.7 mmol) was dissolved in 100 mL of acetic acid followed by the addition of iron powder (6.20 g, 0.11 mol). The reaction mixture was heated to 65° C., stirred for 4 hours and filtered. The filter cake was washed with dichloromethane (100 mL). The filtrate was concentrated under reduced pressure, then added with 100 mL of water and filtered. The filter cake was dried by heating to obtain the crude compound (7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one 43c (7.17 g) as a gray solid, which was used in the next step without further furification.

Workup

filtrationfiltered
washThe filter cake was washed with dichloromethane (100 mL)
concentrationThe filtrate was concentrated under reduced pressure
additionadded with 100 mL of water
filtrationfiltered
customThe filter cake was dried
temperatureby heating

Sources & evidence

ORD record: ord-1cfa8b8742dd4a249103e1d97f09e2c4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691822B2

Reaction notes

Loading…