Sodium Cyanide → HCID 86627799, compound

HRID 645515Notes

Reaction equation

HRID 645515 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:18][CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[N:9][C:10](S(C)(=O)=O)=[N:11][C:12]=1[Cl:13])=[O:6])[CH:2]=[CH2:3].[C-:34]#[N:35].[Na+]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:18][CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[N:9][C:10]([C:34]#[N:35])=[N:11][C:12]=1[Cl:13])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86627800HCID 86627800, compound

Product 1

HCID 86627799HCID 86627799, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Following the synthetic procedure as described in Ref. Example 2, a solution of 4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy]6-chloro-2-methanesulfonylpyrimidine-5-carboxylic acid allyl ester (1.8 mmol) in CH2Cl2 (5 mL) is treated with a solution of NaCN (2.2 mmol) and tetra-n-butylammonium bromide (0.10 mmol) in water (2 mL) for 0.5 h. After usual work-up, the crude material is purified by silica gel chromatography to give 4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy]-6-chloro-2-cyanopyrimidine-5-carboxylic acid allyl ester as colorless oil; 1H-NMR (CDCl3), δ: 1.12-1.73 (9H, m), 1.48 (9H, s), 2.68 (2H, brt), 4.05-4.09 (2H, m), 4.55 (2H, t), 4.87 (2H, dt), 5.33-5.37 (1H, m), 5.41-5.47 (1H, m), 5.98 (1H, ddt).

Workup

  1. customAfter usual work-up, the crude material is purified by silica gel chromatography

Sources & evidence

ORD record
ord-d2e592354e504e8ab713bd913b308928
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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