Dimethylamine → HCID 178483637, compound

HRID 1743790Notes

Reaction equation

HRID 1743790 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17]OS(C)(=O)=O)[CH2:13][CH2:12]2)=[N:6][CH:7]=1.[CH3:23][NH:24][CH3:25].[Na+].[I-]>CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][N:24]([CH3:25])[CH3:23])[CH2:13][CH2:12]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 178505295HCID 178505295, compound

Product 1

HCID 178483637HCID 178483637, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 258 mg (corresponding to 0.41 mmol) of crude trans-Methanesulfonic acid 4-[2-(5-bromo-pyrimidin-2-ylamino)-ethyl]-cyclohexylmethyl ester in 5 ml of methanol was treated with 0.73 ml (4.1 mmol) Dimethylamine (33% in EtOH, 5.6M) and heated at 65° C. for 4 h, a catalytic amount of NaI was added and heated for 16 h. After cooling and evaporation, the residue was extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried (Na2SO4), filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1) gave 105 mg (76%) of trans-(5-Bromo-pyrimidin-2-yl)-[2-(4-dimethylaminomethyl-cyclohexyl)-ethyl]-amine, mp: 108.3–109.5° C.; MS: 341 (MH+, 1Br).

Workup

  1. temperatureheated for 16 h
  2. temperatureAfter cooling
  3. customevaporation
  4. extractionthe residue was extracted with aqueous saturated NaHCO3/Et2O (3×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1)

Sources & evidence

ORD record
ord-e37185306f05435184067b2ebde7d514
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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