Trifluoroacetic acid → HCID 54725631, compound

HRID 458686Notes

Reaction equation

HRID 458686 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18](=[O:21])[N:19]([CH3:20])[C:12]2=[N:11][C:10]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])C1C=CC=CC=1.FC(F)(F)C(O)=O>C(OCC)(=O)C.CCCCCC>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18](=[O:21])[N:19]([CH3:20])[C:12]2=[N:11][C:10]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18442526HCID 18442526, compound

Product 1

HCID 54725631HCID 54725631, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Reaction of intermediate 16, ethyl 3-benzyloxy-9-methyl-4,8-dioxo-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidine-2-carboxylate, (0.413 g, 1.16 mmol) with trifluoroacetic acid (20 ml) as described in the preparation of intermediate 5 gave 0.264 g (85% yield) of the title ester as white crystals, mp 182° C. (ethyl acetate/hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.44 (3H, t, J=7.1 Hz, CH3), 2.80 (2H, t, J=6.8 Hz, CH2), 3.43 (3H, s, NCH3), 4.28 (2H, t, J=6.8 Hz, CH2), 4.46 (2H, q, J=7.1 Hz, OCH2), 10.48 (1H, s, OH). Anal. Calcd for C11H13N3O5: C, 49.43; H, 4.90; N, 15.72. Found: C, 49.39; H, 4.89; N, 15.75.

Sources & evidence

ORD record
ord-a67d0ed523f343eb8bdbf4301894712f
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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