Triphenylphosphine → HCID 57964946, compound

HRID 1931607Notes

Reaction equation

HRID 1931607 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N=C=NC(C)C)(C)C.[C:29]([N:36]1[CH2:41][CH2:40][CH2:39][CH:38](O)[CH2:37]1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[Cl:43][C:44]1[N:49]=[CH:48][N:47]=[C:46]2[NH:50][N:51]=[CH:52][C:45]=12>O1CCCC1>[C:32]([O:31][C:29]([N:36]1[CH2:41][CH2:40][CH2:39][CH:38]([N:50]2[C:46]3=[N:47][CH:48]=[N:49][C:44]([Cl:43])=[C:45]3[CH:52]=[N:51]2)[CH2:37]1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12734DiisopropylcarbodiimideHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidine2×HCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 57964946HCID 57964946, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of triphenylphosphine (1.41 g, 5.4 mmol) in tetrahydrofuran (50 mL) under argon was cooled to 0° C. Diisopropylcarbodiimide (1.06 mL, 5.4 mmol) was added dropwise, followed by 1-Boc-3-hydroxypiperidine (Alfa Aesar, Ward Hill, Mass., USA; 0.92 g, 4.6 mmol) and then 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 30; 0.55 g, 3.6 mmol). The mixture was stirred at room 0° C. for 4 h and the volatiles were then evaporated. The crude product was purified by silica gel chromatography, eluting with 16-20% ethyl acetate/hexanes to give 3-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (135 mg, 11%).

Workup

  1. customthe volatiles were then evaporated
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with 16-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95df97190b87428b865088a3cb857a87
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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