dimethyl pyrimidine-4,6-dicarboxylate → HCID 12997477, compound

HRID 1374731Notes

Reaction equation

HRID 1374731 reaction equation
[N:1]1[C:6]([C:7]([O:9]C)=O)=[CH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[N:3][CH:2]=1.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][C:17]=1[CH3:24]>CN(C=O)C>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][C:7]([C:6]2[N:1]=[CH:2][N:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:5]=2)=[O:9])=[CH:18][C:17]=1[CH3:24]

Participants

4

Reactant 2

HCID 239362dimethyl pyrimidine-4,6-dicarboxylateHCID 2774599(4-Fluoro-3-methylphenyl)methanamine

Product 1

HCID 12997477HCID 12997477, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

8.81 g (0.045 mol) of dimethyl pyrimidine-4,6-dicarboxylate were dissolved in 200 ml of DMF, after which 6.25 g (0.045 mol) of 4-fluoro-3-methylbenzylamine were added and the mixture was stirred at 60° C. for 48 hours (h). The solvent was removed in vacuo and the residue was taken up in ethyl acetate. The organic phase was washed with a saturated solution of sodium hydrogen carbonate and 0.5 N HCl and then dried (MgSO4). After filtering, and evaporating the solvent in vacuo, the residue was stirred up in isopropanol. This resulted in 8.75 g of product, which was subjected to further reaction without any further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic phase was washed with a saturated solution of sodium hydrogen carbonate and 0.5 N HCl
  3. dry with materialdried (MgSO4)
  4. filtrationAfter filtering
  5. customevaporating the solvent in vacuo
  6. stirringthe residue was stirred up in isopropanol

Sources & evidence

ORD record
ord-964b6fb54cc04c4d9c0237ef2451774c
Source dataset
uspto-grants-2007_01
Patent number
US07166609B2

Reaction notes

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