Dibutyltin oxide → HCID 178488418, compound

HRID 1926920Notes

Reaction equation

HRID 1926920 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][CH2:22][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][CH2:22][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 58016841HCID 58016841, compound

Product 1

HCID 178488418HCID 178488418, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Stir 0.098 g (0.23 mmol) 7-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}-heptanenitrile, 0.41 g (3.5 mmol) trimethylsilylazide and 86 mg (0.25 mmol) di-n-butyltin oxide in 5 ml toluene overnight at 80° C. After concentrating by evaporation, take up the residue in water, acidify with dilute hydrochloric acid and extract with methylene chloride. Wash the organic phase with sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. Purify the raw product 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). 61 mg (55% of theor.) of the title compound is obtained as white crystals.

Workup

  1. concentrationAfter concentrating by evaporation
  2. extractionextract with methylene chloride
  3. washWash the organic phase with sodium chloride solution
  4. dry with materialdry over magnesium sulphate
  5. concentrationconcentrate by evaporation
  6. customPurify the raw product 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-dc4bc36d82bf4d2b9be1f882431233c1
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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