N-(2-Hydroxyethyl)aniline → HCID 59333748, compound

HRID 1930585Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16](OS(C(F)(F)F)(=O)=O)[C:17]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[C:39]1([NH:45][CH2:46][CH2:47][OH:48])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CS(C)=O>[OH:48][CH2:47][CH2:46][N:45]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:16]1[C:17]2[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:21][CH2:20][C:18]=2[N:19]=[C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][CH:9]=2)[N:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

tert-Butyl 2-(4-(1-methyl-1H-pyrazol-4-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1 g, 1.80 mmol) and 2-(phenylamino)ethanol (0.228 mL, 1.80 mmol) in dimethylsulfoxide (3 mL) were charged in a thick wall glass, which was sealed and heated under microwave irradiation at 70° C. for 7 h. The solvent was evaporated together with toluene, the crude impregnated in silica gel and purified by flash chromatography (ISCO) using dichloromethane/methanol (0-10%) as eluent and the solvent evaporated under reduced pressure yielding tert-butyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(1-methyl-1H-pyrazol-4-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.882 g, 90%). MS (ESI) (M+H) m/z 542

Workup

customwas sealed
customThe solvent was evaporated together with toluene
custompurified by flash chromatography (ISCO)
customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record: ord-9f235e63a4e0473884d960ea8b678fff
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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