Acrylonitrile → HCID 86653754, compound

HRID 2189048Notes

Reaction equation

HRID 2189048 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([O:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][C@H:27]([OH:31])[CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:11][CH:10]=1.[C:38](#[N:41])[CH:39]=[CH2:40]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3[C:22]([O:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][C@H:27]([O:31][CH2:40][CH2:39][C:38]#[N:41])[CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 23665647Potassium tert-butoxideHCID 86653755HCID 86653755, compound

Product 1

HCID 86653754HCID 86653754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of 10 mg of potassium tert-butoxide in 0.5 ml of THF dropwise to a solution of 150 mg (0.36 mmol) of (+/−)-cis-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}cyclohexanol in 1 ml of acrylonitrile. Stir the reaction mixture with exclusion of light at RT for approx. 2 h. After dilution with dichloromethane, wash successively with 1N hydrochloric acid, satd. sodium hydrogencarbonate solution and satd. sodium chloride solution, and concentrate the organic phase under reduced pressure. After purification of the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 136.9 mg of the target product are obtained (81% of theory).

Workup

  1. washAfter dilution with dichloromethane, wash successively with 1N hydrochloric acid
  2. concentrationsodium chloride solution, and concentrate the organic phase under reduced pressure
  3. customAfter purification of the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 136.9 mg of the target product
  4. customare obtained (81% of theory)

Sources & evidence

ORD record
ord-095c631c109d44b489ddd189d2c3f78f
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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