Sodium Iodide → HCID 178482354, compound

HRID 1743802Notes

Reaction equation

HRID 1743802 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:16])[C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.[H-].[Na+].[Na+].[I-]>CC(N(C)C)=O.O.CCOCC>[Br:1][C:2]1[CH:7]=[N:6][C:5]([N:8]([CH3:16])[C@H:9]2[CH2:10][CH2:11][C@H:12]([O:15][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:13][CH2:14]2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 178482352HCID 178482352, compound

Product 1

HCID 178482354HCID 178482354, compoundYield 4,844.8%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21584184Diethylether waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.2 g (0.7 mmol) of trans-4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexanol and 0.24 g (1.4 mmol) 1-(2-chloroethyl)pyrrolidine hydrochloride in 3.5 ml of DMA was treated at 0° C. with 0.24 g (5.59 mmol) of NaH (55% in oil) in small portions. The reaction was stirred for 30 min at 0° C. After warming up to RT a catalytic amount of NaI was added to the reaction and stirred for 1 h at 80° C. The reaction was cooled and poured into water/Et2O (3×). The organic phase was dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/MeOH 99:1 to 9:1) to yield 13 g (5%) of trans-(5-Bromo-pyrimidin-2-yl)-methyl-[4-(2-pyrrolidin-1-yl-ethoxy)-cyclohexyl]-amine, MS: 383 (MH+, 1Br).

Workup

  1. additionwas added to the reaction
  2. stirringstirred for 1 h at 80° C
  3. temperatureThe reaction was cooled
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (CH2Cl2/MeOH 99:1 to 9:1)

Sources & evidence

ORD record
ord-b9e4146620534256bcde56bc518cb18a
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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