Triphenylphosphine → 3-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1931693Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:34][S:35]([C:38]1[CH:53]=[CH:52][C:41]([O:42][C:43]2[N:48]=[CH:47][N:46]=[C:45]3[NH:49][N:50]=[CH:51][C:44]=23)=[CH:40][CH:39]=1)(=[O:37])=[O:36].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:49]2[C:45]3=[N:46][CH:47]=[N:48][C:43]([O:42][C:41]4[CH:40]=[CH:39][C:38]([S:35]([CH3:34])(=[O:36])=[O:37])=[CH:53][CH:52]=4)=[C:44]3[CH:51]=[N:50]2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Boc-3-hydroxypiperidine (Alfa Aesar, Ward Hill, Mass., USA; 80 mg, 0.4 mmol) and triphenylphosphine (136 mg, 0.52 mmol) were added to a solution of 4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 31; 100 mg, 0.34 mmol) in tetrahydrofuran (1 mL). The mixture was cooled to 0° C., and then diisopropylazodicarboxylate (102 μL, 0.52 mmol) was added. The mixture was stirred overnight, then silica gel (˜500 mg) was added, the solvents were evaporated and the product was eluted from a silica gel column with 50% ethyl acetate/hexanes to give 3-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (10.5 mg, 6.5%) as a solid.

Workup

additionsilica gel (˜500 mg) was added
customthe solvents were evaporated
washthe product was eluted from a silica gel column with 50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-aefacd492a7b4d518bdec825f3cdd990
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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