Tetrabutylammonium Fluoride Trihydrate → HCID 19081616, compound

HRID 963383Notes

Reaction equation

HRID 963383 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH2:25][C:26]3[C:27]([NH2:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=3)[CH:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH2:25][C:26]3[C:27]([NH2:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=3)[CH:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 54384031HCID 54384031, compound

Product 1

HCID 19081616HCID 19081616, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

267 mg of 5-(4'-t-butyl-dimethylsilyloxy-5,6-dimethoxybiphenyl-3-ylmethyl)-pyrimidine-2,4-diamine (Example 2f)) are dissolved in 6 ml of tetrahydrofuran and treated with 361 mg of tetrabutylammonium fluoride trihydrate. The mixture is stirred at room temperature for 1hr. and subsequently concentrated. The residue is chromatographed on MCl-Gel CHP20P (Mitsubishi Corporation) with water/acetonitrile 4:1. 73 mg (36%) of 5-(4'-hydroxy-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a colourless solid. M.p. 233°.

Workup

  1. concentrationand subsequently concentrated
  2. customThe residue is chromatographed on MCl-Gel CHP20P (Mitsubishi Corporation) with water/acetonitrile 4:1

Sources & evidence

ORD record
ord-2a88522342624a458ffece1da45d6bb3
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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