Dimethylamine → HCID 178483438, compound

HRID 1743776Notes

Reaction equation

HRID 1743776 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:24])[C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][CH2:18]OS(C)(=O)=O)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH3:25][NH:26][CH3:27]>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][CH2:18][N:26]([CH3:27])[CH3:25])[CH2:11][CH2:10]2)[CH3:24])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178482348HCID 178482348, compound

Product 1

HCID 178483438HCID 178483438, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 211 mg (0.51 mmol) of crude trans-Methanesulfonic acid 4-{4-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-but-3-ynyl ester in 5 ml of methanol was treated with 0.91 ml (5.1 mmol) Dimethylamine (33% in EtOH, 5.6M) and heated at 65° C. for 4 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 95:5) gave 141 mg (76%) of trans-(5-Bromo-pyrimidin-2-yl)-[4-(4-dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-amine, MS: 365 (MH+, 1Br).

Workup

  1. temperatureAfter cooling
  2. customevaporation
  3. extractionthe residue was extracted with aqueous saturated NaHCO3/Et2O (3×)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 95:5)

Sources & evidence

ORD record
ord-9d11bcac7d744c9486e396371a21705f
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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