Triphenylphosphine → Tert-butyl 2-(4-((7-isobutyl-5-methyl-4,6-dioxo-3-(phenylamino)-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidin-2-yl)methyl)phenyl)piperidine-1-carboxylate

HRID 81419Notes

Reaction equation

O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:41]([N:45]1[C:50]2=[N:51][NH:52][C:53]([NH:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[C:49]2[C:48](=[O:61])[N:47]([CH3:62])[C:46]1=[O:63])[CH:42]([CH3:44])[CH3:43].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:41]([N:45]1[C:50]2=[N:51][N:52]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH:9]4[CH2:14][CH2:13][CH2:12][CH2:11][N:10]4[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:5][CH:4]=3)[C:53]([NH:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)=[C:49]2[C:48](=[O:61])[N:47]([CH3:62])[C:46]1=[O:63])[CH:42]([CH3:44])[CH3:43]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-butyl 2-(4-(hydroxymethyl)phenyl)piperidine-1-carboxylate (47 mg, 0.16 mmol) is dissolved in 1 mL of anhydrous THF, and then triphenylphosphine (42 mg, 0.16 mmol) is added, followed by 7-isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (50 mg, 0.16 mmol). The mixture is cooled to −78° C., and then DIAD (95%, 50 μL) is added slowly. After the reaction is complete, the mixture is purified on a basic alumina column to give 76 mg of product (yield: 81%). MS (ESI) m/z 587.3 [M+H]+.

Workup

customthe mixture is purified on a basic alumina column

Sources & evidence

ORD record: ord-bddf2e399bd94b8985cc4f2d40891a02
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846693B2

Reaction notes

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