Dimethylamine → HCID 178483457, compound

HRID 1743771Notes

Reaction equation

HRID 1743771 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:23])[C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17]OS(C)(=O)=O)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH3:24][NH:25][CH3:26]>CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][N:25]([CH3:26])[CH3:24])[CH2:11][CH2:10]2)[CH3:23])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178482350HCID 178482350, compound

Product 1

HCID 178483457HCID 178483457, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 125 mg (corresponding to 0.30 mmol) of crude trans-Methanesulfonic acid 3-{4-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-ynyl ester in 3 ml of methanol was cooled (0° C.), treated with 0.54 ml (3 mmol) of Dimethylamine (33% in EtOH 5.6M) and stirred for 20 h at RT. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 97.5:2.5) gave 65 mg (62%) of pure trans-(5-Bromo-pyrimidin-2-yl)-[4-(3-dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-amine, mp: 83–84° C., dec.; MS: 351 (MH+, 1Br).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 97.5:2.5)

Sources & evidence

ORD record
ord-8ae999b23f784c058927f2e597be0b65
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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