Sodium hydride → HCID 57496307, compound

HRID 1864126Notes

Reaction equation

HRID 1864126 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[H-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]3=[N:28][CH:29]=[N:30][C:31](Cl)=[C:26]3[CH:25]=[N:24]2)=[CH:19][CH:18]=1>C1COCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][C:31]2[N:30]=[CH:29][N:28]=[C:27]3[N:23]([C:20]4[CH:19]=[CH:18][C:17]([Br:16])=[CH:22][CH:21]=4)[N:24]=[CH:25][C:26]=23)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 113927311-(4-bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylate

Product 1

HCID 57496307HCID 57496307, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (727 mg, 3.88 mmol), and sodium hydride (465 mg, 19.4 mmol) in THF (12 mL) was stirred for 30 min at 60° C. 1-(4-Bromo-phenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine was added to the mixture at room temperature and stirred for 1.0 hr at RT. The reaction was quenched with water and the product extracted in ethyl acetate. The organic layer was concentrated in vacuo to provide Compound A220 as a white solid (1.3 g, 81%). 1H NMR (CDCl3, 400MHz) δ 1.19 (d, 6H), 1.73-1.85 (m, 2H), 1.98-2.08 (m, 2H), 3.26-3.34 (m, 2H), 3.78-3.87 (m, 2H), 4.88 (h, 1H), 5.54 (h, 1H), 7.57 (d, 2H), 8.07 (d, 2H), 8.13 (s, 1H), 8.55 (s, 1H). Exact mass calculated for C20H22BrN5O3 460.3, found 462.3 (MH+).

Workup

  1. stirringstirred for 1.0 hr at RT
  2. customThe reaction was quenched with water
  3. extractionthe product extracted in ethyl acetate
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-9ec0de0b65334207be9eec4ac939d4bd
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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