Dibutyltin oxide → HCID 178488420, compound

HRID 1926927Notes

Reaction equation

HRID 1926927 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]#[N:26])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:5][CH:4]=1.C[Si]([N:37]=[N+:38]=[N-:39])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]4[NH:39][N:38]=[N:37][N:26]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 580168795-(4-Methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]pyrimidine-4-amine

Product 1

HCID 178488420HCID 178488420, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Stir 137 mg (0.32 mmol) 5-(4-methoxyphenyl)-6-phenyl-N-{3-[2-cyanoethoxy]propyl}furo[2,3-d]-pyrimidine-4-amine, 552 mg (4.8 mmol) trimethylsilylazide and 119 mg (0.48 mmol) di-n-butyltin oxide in 10 ml toluene overnight at 80° C. Then cool the mixture and concentrate by evaporation. Dissolve the residue that remains in methylene chloride and wash with water and sodium chloride solution. Dry the organic phase over magnesium sulphate and concentrate in the rotary evaporator at reduced pressure. Purify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile). 48.6 mg (32% of theor.) of the title compound is obtained as a colourless solid.

Workup

  1. temperatureThen cool the mixture
  2. concentrationconcentrate by evaporation
  3. dissolutionDissolve the residue that
  4. washwash with water and sodium chloride solution
  5. dry with materialDry the organic phase over magnesium sulphate
  6. concentrationconcentrate in the rotary evaporator at reduced pressure
  7. customPurify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile)

Sources & evidence

ORD record
ord-5f353c587520493aa5532de51b1f4407
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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