HCID 67441493, compound → HCID 58478360, compound

HRID 1517252Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[C:26](=[O:27])[N:25]([O:28][CH3:29])[C:14]2[N:15]=[C:16]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[N:17]=[CH:18][C:13]=2[CH:12]=1>CCO.Cl.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]2[C:26](=[O:27])[N:25]([O:28][CH3:29])[C:14]3[N:15]=[C:16]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[N:17]=[CH:18][C:13]=3[CH:12]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(2-chloro-4-nitrophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one (8.36 mmol) in EtOH (300 mL) and conc. hydrochloric acid (20 mL), iron powder (91 mmol) was added and the mixture was stirred at 80° C. for 2 h. The mixture was then allowed to cool to room temperature and filtered through a pad of Celite. The filtrate was diluted with EtOAc (300 mL) and washed with sat. aq. NaHCO3 (300 mL). The aqueous layer was backextracted with EtOAc (8×150 mL). The organic layers were combined and washed with brine (1×300 mL). Drying of the organic layer over Na2SO4, filtration and evaporation of the solvent gave 6-(4-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one as a solid (43%).

Workup

temperatureto cool to room temperature
filtrationfiltered through a pad of Celite
additionThe filtrate was diluted with EtOAc (300 mL)
washwashed with sat. aq. NaHCO3 (300 mL)
washwashed with brine (1×300 mL)
dry with materialDrying of the organic layer over Na2SO4, filtration and evaporation of the solvent

Sources & evidence

ORD record: ord-de9ad6f4449844c6a5fe2c54498220e5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232283B2

Reaction notes

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