Dimethylamine → HCID 178483458, compound

HRID 1743773Notes

Reaction equation

HRID 1743773 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]([CH2:15][CH2:16][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]([CH2:15][CH2:16][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 674Dimethylamine2×HCID 178482351HCID 178482351, compound

Product 1

HCID 178483458HCID 178483458, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 209 mg (corresponding to 0.50 mmol) of crude trans-Methanesulfonic acid 3-{4-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-propyl ester in 5 ml of methanol was treated with 0.89 ml (5 mmol) Dimethylamine (33% in EtOH, 5.6M) and stirred over night at RT. After the addition of 0.45 ml (2.5 mmol) Dimethylamine (33% in EtOH, 5.6M), the reaction was stirred for 66 h, then heated at 70° C. for 2 h, cooled, 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 97:3 to 94:6) gave 157 mg (88%) of trans-(5-Bromo-pyrimidin-2-yl)-[4-(3-dimethylamino-propyl)-cyclohexyl]-methyl-amine, MS: 355 (MH+, 1Br).

Workup

  1. stirringthe reaction was stirred for 66 h
  2. temperatureheated at 70° C. for 2 h
  3. temperaturecooled
  4. customevaporated
  5. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  6. dry with materialThe organic phase was dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 97:3 to 94:6)

Sources & evidence

ORD record
ord-99dd65833b30428580dc139f571d8b28
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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