Selenium Dioxide → Methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-formyl-6-(1-methyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate

HRID 515979Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([CH3:22])[C:19]([C:23]([O:25][CH3:26])=[O:24])=[C:18]([C:27]2[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Se](=O)=[O:34]>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([CH:22]=[O:34])[C:19]([C:23]([O:25][CH3:26])=[O:24])=[C:18]([C:27]2[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 25 mL round bottom flask was added methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-methyl-6-(1-methyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate (0.17 g, 0.382 mmol), selenium dioxide (0.085 g, 0.765 mmol) and dioxane. The reaction mixture was heated at 100° C. overnight, cooled to RT, and filtered through a bed of Celite 545, which was rinsed with MeOH. The solvent was removed to give the title compound as yellowish-brown foam, which was used in the next step without further purification (245 mg).

Workup

temperaturecooled to RT
filtrationfiltered through a bed of Celite 545, which
washwas rinsed with MeOH
customThe solvent was removed

Sources & evidence

ORD record: ord-27900a96cfb8493ba4f97682a2cacf4f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108970B2

Reaction notes

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