Heptane → 4-(2-Methoxypyrimidin-5-yl)glutaric anhydride

HRID 1182348Notes

Reaction equation

HRID 1182348 reaction equation
C(CC([C:10]1[CH:11]=[N:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=1)CC(O)=O)(O)=O.F[C:19](F)(F)[C:20]([O:22][C:23](=[O:28])[C:24](F)(F)F)=[O:21].[CH3:31]CCCCCC>C1COCC1>[CH3:17][O:16][C:13]1[N:14]=[CH:15][C:10]([CH:24]2[C:23](=[O:28])[O:22][C:20](=[O:21])[CH2:19][CH2:31]2)=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 9845Trifluoroacetic anhydrideHCID 112764933-(2-methoxy-5-pyrimidinyl)Pentanedioic acid

Product 1

HCID 866062674-(2-Methoxypyrimidin-5-yl)glutaric anhydrideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Carboxy-3-(2-methoxypyrimidin-5-yl)butanoic acid (11.5 kg) was treated with trifluoroacetic anhydride (12.1 kg) in THF (58 L) at 50-55° C. for several hours. Slow addition of heptane (195 L) followed by cooling to ambient temperature resulted in the crystallization of the title compound; 94% yield.

Sources & evidence

ORD record
ord-a7b321e4eb9942c587e4c2540fe21264
Source dataset
uspto-grants-2007_10
Patent number
US07288655B2

Reaction notes

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