tert-Butanol → 7-Phenyl-5H-pyrimido[5,4-d][2]benzazepin-5-one oxime

HRID 248349Notes

Reaction equation

HRID 248349 reaction equation
CC(C)([O-])C.[K+].C(O)(C)(C)C.[C:12]1([C:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22]3[N:29]=[CH:30][N:31]=[CH:32][C:21]=3[CH2:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N:33](OCCC(C)C)=[O:34]>O1CCCC1>[N:33](=[C:20]1[C:21]2[CH:32]=[N:31][CH:30]=[N:29][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:19]1)[OH:34]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8053Isoamyl NitriteHCID 19763354HCID 19763354, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 1360725937-Phenyl-5H-pyrimido[5,4-d][2]benzazepin-5-one oxime

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a suspension of potassium tert-butoxide (24.9 g, 222 mmole) in 600 ml of dry tetrahydrofuran is added 200 ml of dry tert-butylalcohol at -20° C. under nitrogen. To this solution is then added, via addition funnel, 7-phenyl-5H-pyrimido[5,4-d][2]-benzazepine (25 g) in 260 ml of tetrahydrofuran. The resulting solution is stirred for about 2 hours at -20° C. and treated with 17.4 ml (130 mmole) of isoamyl nitrite. The reaction mixture is warmed to 0° C. over approximately 15 minutes and quenched with the addition of 60 ml of cold water and 20 ml of glacial acetic acid. All solvents are removed under reduced pressure and the residue is partitioned between ethyl acetate (600 ml) and brine (100 ml). The phases are separated and the organic extracts are dried (Na2SO4), concentrated, and triturated with ether.

Workup

  1. additionTo this solution is then added, via addition funnel
  2. temperatureThe reaction mixture is warmed to 0° C. over approximately 15 minutes
  3. customquenched with the addition of 60 ml of cold water and 20 ml of glacial acetic acid
  4. customAll solvents are removed under reduced pressure
  5. customthe residue is partitioned between ethyl acetate (600 ml) and brine (100 ml)
  6. customThe phases are separated
  7. dry with materialthe organic extracts are dried (Na2SO4)
  8. concentrationconcentrated
  9. customtriturated with ether

Sources & evidence

ORD record
ord-ce3a8da856224bba9a372ceebd806b16
Source dataset
uspto-grants-1993_05
Patent number
US05210082

Reaction notes

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