Potassium Iodide → HCID 58280114, compound

HRID 2189050Notes

Reaction equation

HRID 2189050 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][CH2:25][CH:26]4[CH2:30][CH2:29][CH2:28][NH:27]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][CH2:25][CH:26]4[CH2:30][CH2:29][CH2:28][N:27]4[CH2:2][CH2:3][CH2:4][C:5]#[N:6])=[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-BromobutyronitrileHCID 81531DiisopropylethylamineHCID 58280184HCID 58280184, compound

Product 1

HCID 58280114HCID 58280114, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 221.2 mg (0.996 mmol) of 4-bromobutyronitrile at RT to a solution of 300 mg (0.747 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-4-(pyrrolidin-2-ylmethoxy)furo[2,3-d]pyrimidine, 0.37 ml (2.24 mmol) of diisopropylethylamine and 12.4 mg of potassium iodide in 3 ml of THF. Stir the mixture under reflux for 6 h. 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 drying the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 178.1 mg of the target product are obtained (50.9% of theory).

Workup

  1. temperatureunder reflux for 6 h
  2. washwash with satd
  3. customsodium hydrogencarbonate solution, remove the organic phase
  4. dry with materialdry over sodium sulphate
  5. concentrationconcentrate under reduced pressure
  6. dry with materialAfter drying the residue by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 178.1 mg of the target product
  7. customare obtained (50.9% of theory)

Sources & evidence

ORD record
ord-8a871d328918430b89d7c51104035b41
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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