Potassium Iodide → HCID 58280257, compound

HRID 2189047Notes

Reaction equation

HRID 2189047 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C1COCC1.ClCCl>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3[C:22]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 214124-Bromobutyronitrile2×HCID 81531Diisopropylethylamine2×HCID 58280169HCID 58280169, compound

Product 1

HCID 58280257HCID 58280257, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 147.5 mg (0.996 mmol) of 4-bromobutyronitrile at RT to a mixture of 200 mg (0.498 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-4-(piperidin-3-yloxy)furo[2,3-d]pyrimidine, 0.25 ml (1.5 mmol) of diisopropylethylamine and 8.3 mg of potassium iodide in 2 ml of THF. The mixture is stirred under reflux for 10 h. After adding a further 0.25 ml (1.5 mmol) of diisopropylethylamine and 147.5 mg (0.996 mmol) of 4-bromobutyronitrile, continue to stir under reflux overnight. After cooling to RT, dilute with dichloromethane, wash with satd. sodium hydrogencarbonate solution, remove the organic phase, dry over sodium sulphate and concentrate under reduced pressure. After purifying the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient) 189 mg of the target product are obtained (81.1% of theory).

Workup

  1. temperatureunder reflux for 10 h
  2. stirringto stir
  3. temperatureunder reflux overnight
  4. washwash with satd
  5. customsodium hydrogencarbonate solution, remove the organic phase
  6. dry with materialdry over sodium sulphate
  7. concentrationconcentrate under reduced pressure
  8. customAfter purifying the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient) 189 mg of the target product
  9. customare obtained (81.1% of theory)

Sources & evidence

ORD record
ord-5caeee1c1e654ac0998c6972805f6b4f
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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