Benzyl Alcohol → 4-(benzyloxy)-N-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 1930556Notes

Reaction equation

C(OC([N:8]1[CH2:30][CH2:29][C:11]2[N:12]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:28][CH:27]=[N:26][CH:25]=4)=[CH:20][CH:19]=3)[N:14]=[C:15]([OH:16])[C:10]=2[CH2:9]1)=O)(C)(C)C.[C:31]1([CH2:37]O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.Cl>C1COCC1>[CH2:37]([O:16][C:15]1[C:10]2[CH2:9][NH:8][CH2:30][CH2:29][C:11]=2[N:12]=[C:13]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[O:28][CH:27]=[N:26][CH:25]=3)=[CH:22][CH:23]=2)[N:14]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl-4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.2 g, 0.49 mmol, Example 3d), phenylmethanol (0.063 ml, 0.61 mmol) and triphenylphosphine (0.160 g, 0.61 mmol) in THF (5 mL) was stirred for 10 min. Diisopropyl azodicarboxylate (0.119 mL, 0.61 mmol) was added and reaction was stirred at 50° C. over night. HCl (2M aq, 2 mL) was added and the solution was heated to 75° C. for 1 h, allowing THF to evaporate. The remaining solvent was evaporated under reduced pressure. The crude product was dissolved in MeOH/DMSO and purified on preparative HPLC to give 4-(benzyloxy)-N-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.089 g, 39.7%).

Workup

customreaction
temperaturethe solution was heated to 75° C. for 1 h
customto evaporate
customThe remaining solvent was evaporated under reduced pressure
dissolutionThe crude product was dissolved in MeOH/DMSO
custompurified on preparative HPLC

Sources & evidence

ORD record: ord-f9b1ae7b517841ce9db0c610e1a53248
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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