Dibutyltin oxide → HCID 178488417, compound

HRID 1926918Notes

Reaction equation

HRID 1926918 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][C:24]#[N:25])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:5][CH:4]=1.C[Si]([N:36]=[N+:37]=[N-:38])(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][C:24]4[NH:38][N:37]=[N:36][N:25]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 580169446-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanenitrile

Product 1

HCID 178488417HCID 178488417, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Stir 1.00 g (2.4 mmol) 6-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanenitrile, 4.19 g (26.3 mmol) trimethylsilylazide and 0.91 g (3.6 mmol) di-n-butyltin oxide in 50 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×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 10% acetonitrile, 3-50 min 10%→98% acetonitrile, 50-55 min 98% acetonitrile). Crystallize the combined product fractions from diethyl ether and dry overnight at 50° C. in a vacuum drying cabinet. 598 mg (54% of theor.) of the title compound is obtained as almost 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×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 10% acetonitrile, 3-50 min 10%→98% acetonitrile, 50-55 min 98% acetonitrile)
  7. customCrystallize the combined product fractions from diethyl ether
  8. customdry overnight at 50° C. in a vacuum
  9. customdrying cabinet

Sources & evidence

ORD record
ord-8db6280f90e44b96a989e86b5c57ce25
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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