Iodine → HCID 71746453, compound

HRID 570546Notes

Reaction equation

HRID 570546 reaction equation
N[C:2]1[C:3]2[C:26]([CH3:28])([CH3:27])[C:25](=[O:29])[NH:24][C:4]=2[N:5]=[C:6]([C:8]2[C:9]3[CH2:23][CH2:22][CH2:21][C:10]=3[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[N:12]=2)[N:7]=1.N(OCCC(C)C)=O.[I:38]I.[I-].[Cs+]>C(COC)OC.[Cu]I>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:11]1[C:10]2[CH2:21][CH2:22][CH2:23][C:9]=2[C:8]([C:6]2[N:7]=[C:2]([I:38])[C:3]3[C:26]([CH3:27])([CH3:28])[C:25](=[O:29])[NH:24][C:4]=3[N:5]=2)=[N:12]1

Participants

7

Reactant 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 712856274-Amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 71746453HCID 71746453, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

285 mg (0.68 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were initially charged in absolute dimethoxyethane, and 800 mg (6.83 mmol) of isopentyl nitrite, 87 mg (0.34 mmol) of iodine, 39 mg (0.21 mmol) of copper(I) iodide and 177 mg (0.68 mmol) of caesium iodide were added. The mixture was stirred at 100° C. for 40 min. The mixture was concentrated on a rotary evaporator, and the residue was taken up in dichloromethane and washed with 5% aqueous sodium thiosulphate solution and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, concentrated and purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% acetic acid, gradient 20:80→100:0). 148 mg (40% of theory) of the target compound were obtained.

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. washwashed with 5% aqueous sodium thiosulphate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated
  5. custompurified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% acetic acid, gradient 20:80→100:0)
  6. custom148 mg (40% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-7d96a6c9ccad4a70a41a8454a5dfd1c3
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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