TBAF tetrahydrofuran → HCID 178480848, compound

HRID 2421004Notes

Reaction equation

HRID 2421004 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]3[C:15]([O:29]CC[Si](C)(C)C)=[N:16][C:17]([NH:20][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[N:18][CH:19]=3)=[N:11][N:10]=2)[CH2:4][CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[OH:29][C:15]1[C:14]([C:12]2[O:13][C:9]([CH2:8][N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[N:10][N:11]=2)=[CH:19][N:18]=[C:17]([NH:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)[N:16]=1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 67250567HCID 67250567, compound

Product 1

HCID 178480848HCID 178480848, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 80 mL of THF, 5-[5-(4-methylpiperazinyl)methyl[1,3,4]oxadiazol-2-yl]-2-[2-(4-pyridyl)ethylamino]-4-(2-trimethylsilylethoxy)pyrimidine (3.83 g, 7.71 mmol) obtained in Step 3 was dissolved, then TBAF-THF solution (1.0 mol/L, 15.8 mL, 15.8 mmol) was added thereto, followed by stirring at a temperature between room temperature and 50° C. in total of 5 hours. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol). Then, the residue was crystallized from hexane/ethyl acetate to give 4-hydroxy-5-[5-(4-methylpiperazinyl)methyl[1,3,4]oxadiazol-2-yl]-2-[2-(4-pyridyl)ethylamino]pyrimidine [Compound (AB) in which R2B is [2-(4-pyridyl)ethylamino] and —X—Y—Z— is

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol)
  3. customThen, the residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-039f0996d26d46f0bca3c2d38e32bf04
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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