Dimethylamine → HCID 178483455, compound

HRID 1743798Notes

Reaction equation

HRID 1743798 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]#[C:18][CH2:19]OS(C)(=O)=O)[CH2:13][CH2:12]2)[CH3:9])=[N:6][CH:7]=1.[Na+].[I-].[CH3:27][NH:28][CH3:29]>CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]#[C:18][CH2:19][N:28]([CH3:29])[CH3:27])[CH2:13][CH2:12]2)[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 178484024HCID 178484024, compound

Product 1

HCID 178483455HCID 178483455, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 323 mg (corresponding to 0.49 mmol) of trans-Methanesulfonic acid 3-(4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexyl)-prop-2-ynyl ester in 5 ml of methanol was cooled (0° C.), treated with a catalytic amount of NaI, 0.88 ml (4.94 mmol) of Dimethylamine (33% in EtOH 5.6M) and stirred for 16 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 40:1) gave 137 mg (76%) of pure trans-(5-Bromo-pyrimidin-2-yl)-[4-(3-dimethylamino-prop-1-ynyl)-cyclohexylmethyl]-methyl-amine, mp: 71–72° C.; MS: 365 (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 40:1)

Sources & evidence

ORD record
ord-7336e1c118664852aab18650ba51a26e
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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