Ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate → Ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

HRID 458683Notes

Reaction equation

HRID 458683 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:12]2=[N:11][C:10]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:12]2=[N:11][C:10]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

3

Reactant 1

HCID 18442533Ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

Product 1

HCID 54725632Ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylateYield 83.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Reaction of intermediate 12, ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate, (0.500 g, 1.46 mmol) with trifluoroacetic acid (20 ml) as described in the preparation of intermediate 5 gave 0.308 g (83% yield) of the title ester as white crystals; mp 229–230° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.49 (3H, t, J=7.1 Hz, CH3), 3.31 (3H, s, NCH3), 4.51 (2H, q, J=7.2 Hz, OCH2), 4.55 (2H, s, CH2), 10.84 (2H, s, OH). Anal. Calcd for C10H11N3O5: C, 47.43; H, 4.37; N, 16.59. Found: C, 47.22; H, 4.13; N, 16.48.

Sources & evidence

ORD record
ord-2d442141a24a48d69219ae689f57abbe
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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