Benzyl Alcohol → HCID 67538861, compound

HRID 1192323Notes

Reaction equation

HRID 1192323 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](I)=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:41]([OH:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>[Cu]I.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([O:48][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 67538830HCID 67538830, compound

Product 1

HCID 67538861HCID 67538861, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A sealed tube charged with 4-(5-Iodo-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (780 mg, 2.00 mmol), CuI (38 mg, 0.20 mmol), 1,10-phenathroline (72 mg, 0.4 mmol), Cs2CO3 (912 mg, 2.8 mmol), benzyl alcohol (0.62 mL, 6.0 mmol) and toluene (2 mL) was heated at 110° C. for 40 hours. The resulting suspension was cooled to room temperature and filtered through a silica gel pad, eluting with EtOAc. Evaporation of the solvent followed by flash chromatography on silica gel (10:1 hexanes/EtOAc) provided 4-(5-benzyloxypyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.640 g, 86%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.36 (s, 1H), 7.99 (s, 1H), 7.39 (m, 5H), 5.08 (s, 2H), 3.73 (m, 4H), 3.48 (m, 4H), 1.47 (s, 9H). LCMS (APCI+) m/z 371 [M+H]+; Rt=2.52 minutes.

Workup

  1. temperatureThe resulting suspension was cooled to room temperature
  2. filtrationfiltered through a silica gel pad
  3. washeluting with EtOAc
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2fb6781780ae4c5f8fe90d96d58b87d2
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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