Triethylsilane → HCID 178505863, compound

HRID 552118Notes

Reaction equation

HRID 552118 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[N:10][CH:11]=2.[SiH](CC)(CC)CC>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:9]2[N:8]=[C:7]3[C:12]([N:13]=[C:14]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[NH:6]3)=[CH:11][N:10]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 58441997HCID 58441997, compound

Product 1

HCID 178505863HCID 178505863, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 46 mg (0.1 mmol, 1.0 eq.) of 9-(2,4-dimethoxybenzyl)-N-(4-fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine (I-17) in 0.6 mL of methylene chloride and 2.4 mL of TFA was stirred at room temperature for 4 h. A portion of 1 mL of Et3SiH was added and the resulting reaction mixture stirred at room temperature for an additional 1 h. The volatiles were removed in vacuo and the residue purified by semi-preparative HPLC to provide 7.3 mg (24%) of N-(4-fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine (I-18).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were removed in vacuo
  3. customthe residue purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-7569a7d2ef994c03a10ad432dbd64aa2
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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