Water → tert-butyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930534Notes

Reaction equation

[C:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:24]=[C:25](OS(C(F)(F)F)(=O)=O)[C:26]4[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29][C:27]=4[N:28]=3)=[CH:18][CH:17]=2)=[CH:14][N:13]=[CH:12]1.O>CS(C)=O>[OH:10][CH2:9][CH2:8][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:25]1[C:26]2[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29][C:27]=2[N:28]=[C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([C:15]3[O:11][CH:12]=[N:13][CH:14]=3)=[CH:21][CH:20]=2)[N:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2-(Phenylamino)ethanol (0.051 g, 0.37 mmol) was added to tert-butyl 2-(4-(oxazol-5-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.2 g, 0.37 mmol, Example 1b) in DMSO (3 mL). The reaction mixture was heated in a microwave reactor at 70° C. for 3 h. Water (1 mL) was added to the solution and the precipitate was washed with water and filtered to give tert-butyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (150 mg, 77%). No further purification. MS (ESI+)/(ESI−) m/z 529/527

Workup

washthe precipitate was washed with water
filtrationfiltered

Sources & evidence

ORD record: ord-970073b353b84590b65f44327164f120
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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