Hydrochloric Acid → N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930538Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:21]=[C:22](OS(C(F)(F)F)(=O)=O)[C:23]4[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26][C:24]=4[N:25]=3)=[CH:15][CH:14]=2)=[CH:11][N:10]=[CH:9]1.Cl>CS(C)=O>[O:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:21]=[C:22]([NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:23]4[CH2:29][NH:28][CH2:27][CH2:26][C:24]=4[N:25]=3)=[CH:15][CH:14]=2)=[CH:11][N:10]=[CH:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

Aniline (0.017 mL, 0.18 mmol) was added to tert-butyl 2-(4-(oxazol-5-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.1 g, 0.18 mmol, Example 1b) in DMSO (4 mL). The solution was heated in a microwave reactor at 80° C. for 1 h. HCl (2M aq, 1.5 mL) was added and the reaction was stirred in an open vessel at 76° C. for 30 min. The reaction was allowed to cool and DMSO was added to the solution. The product was purified by preparative HPLC to give N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (0.017 g, 24%).

Workup

temperatureto cool
customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-0c0498569f0a420dae215e688573dd81
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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