Diisopropylethylamine → HCID 178484083, compound

HRID 2118243Notes

Reaction equation

HRID 2118243 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1.Cl.CCN(C(C)C)C(C)C.Br[C:24]1[N:29]=[CH:28][C:27]([Br:30])=[CH:26][N:25]=1>CC(N(C)C)=O>[Br:30][C:27]1[CH:26]=[N:25][C:24]([N:2]([CH2:3][C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]2)[CH3:1])=[N:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109555882,5-DibromopyrimidineHCID 178484084HCID 178484084, compound

Product 1

HCID 178484083HCID 178484083, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.42 g (2.0 mmol) of trans-4-methylaminomethyl-cyclohexanecarboxylic acid•HCl, 1.85 mL (1.1 mmol) of Huenig's base and 0.57 g (2.4 mmol) of 2,5-dibromo-pyrimidine [Brown and Arantz, J. Chem. Soc. C Issue 10, 1889-1891 (1971)] in 2 mL of DMA was placed in the microwave and heated to 120° C. for 1 h. The solvent was evaporated, partitioned between Et2O (×3)/aqueous 10% KH2PO4, dried over Na2SO4 and evaporated to yield 0.604 g (92%) of trans-4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid, MS: 326 (M−H−, 1Br), MP: 172-174° C.

Workup

  1. customThe solvent was evaporated
  2. custompartitioned between Et2O (×3)/aqueous 10% KH2PO4
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-f6d8bc2225a84289be204cc0975b4c0d
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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