Ethylene Glycol → HCID 178488423, compound

HRID 1926926Notes

Reaction equation

HRID 1926926 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O: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([Sn](=O)CCCC)CCC.C[Si]([N:46]=[N+:47]=[N-:48])(C)C.C(O)CO>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]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]4[NH:48][N:47]=[N:46][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

6

Reactant 4

HCID 174Ethylene GlycolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 580168076-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}hexanenitrile

Product 1

HCID 178488423HCID 178488423, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Stir 1.00 g (2.1 mmol) 6-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}hexanenitrile, 0.79 g (3.2 mmol) di-n-butyltin oxide and 3.68 g (32 mmol) trimethylsilylazide in 44 ml toluene overnight at 80° C. Then add 1 ml ethylene glycol, stir for 1 h under reflux and then concentrate by evaporation. Take up the residue in ethyl acetate, wash with dilute hydrochloric acid and with sodium chloride solution, dry, 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 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). Crystallize the combined product fractions from diethyl ether. 372 mg (38% of theor.) of the title compound is obtained as beige crystals.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrate by evaporation
  3. washwash with dilute hydrochloric acid and with sodium chloride solution
  4. customdry
  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 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)
  7. customCrystallize the combined product fractions from diethyl ether

Sources & evidence

ORD record
ord-2d333a30e7f14bcabc74384c0ab97a49
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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