Water → 4-(5-bromo-2-(2-methyl-1H-imidazol-1-yl)pyrimidin-4-yl)morpholine-3-carboxylic acid

HRID 1631737Notes

Reaction equation

HRID 1631737 reaction equation
[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([OH:17])=[O:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:18][C:19]1[NH:20][CH:21]=[CH:22][N:23]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CC(N(C)C)=O>[ClH:8].[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([OH:17])=[O:16])=[N:4][C:5]([N:20]2[CH:21]=[CH:22][N:23]=[C:19]2[CH3:18])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 86670107HCID 86670107, compound

Product 2

HCID 313Hydrochloric AcidHCID 681948754-(5-bromo-2-(2-methyl-1H-imidazol-1-yl)pyrimidin-4-yl)morpholine-3-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (PREPARATION x30, 1 g, 3.12 mmol), 2-methyl-1H-imidazole (0.54 g, 6.55 mmol) and Cs2CO3 (4 g, 12 mmol) in DMA (20 mL) was stirred at 120° C. for 2 days. Water was added and the mixture was concentrated, resulting in precipitation of solids. The solids were collected to give an HCl salt of the title compound as an off-white solid (0.47 g, 45%). 1H NMR (400 MHz, CD3OD) δ 2.95 (s, 3H), 3.96-3.61 (m, 4H), 4.42-4.38 (m, 2H), 5.17-5.15 (m, 1H), 7.50 (d, J=2.0 Hz, 1H), 8.14 (d, J=2.0 Hz, 1H), 8.59 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C13H14BrN5O3, 368. found, 368.

Workup

  1. concentrationthe mixture was concentrated
  2. customresulting in precipitation of solids
  3. customThe solids were collected

Sources & evidence

ORD record
ord-4d65a26a646f48dfb143039d523315da
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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