Trimethylsilyl isocyanate → HCID 58739265, compound

HRID 720649Notes

Reaction equation

HRID 720649 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[C:11](=[O:25])[N:10]([CH2:26][CH2:27][CH2:28][CH3:29])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.C[Si]([N:36]=[C:37]=[O:38])(C)C>ClCCl.CN(C)C=O>[CH2:26]([N:10]1[C:9]2[N:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:37]([NH2:36])=[O:38])=[CH:31][CH:30]=3)[NH:15][C:14]=2[C:13](=[O:16])[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:11]1=[O:25])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 218917201-(2-fluorobenzyl)-8-(4-aminobenzyl)-3-butyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 58739265HCID 58739265, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

8-(4-Amino-benzyl)-3-butyl-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione (25 mg, 0.06 mmol) was dissolved in 95:5 dichloromethane/N,N-dimethylformamide (2 mL), and treated with trimethylsilyl isocyanate (Aldrich) (47 μl, 0.3 mmol). The reaction was stirred at room temperature for 18 h. The reaction was then concentrated under reduced pressure and the residue was purified by reverse phase HPLC to afford the desired product. LCMS, m/z(M+H)=464.98.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4ca2d64adc454c0fa6100ce6a2bfb1d0
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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