HCID 135970954, compound → HCID 135970953, compound

HRID 458681Notes

Reaction equation

HRID 458681 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[NH:24][C:23](=[O:25])[CH2:22][CH2:21][N:9]2[C:10](=[O:20])[C:11]=1[O:12]CC1C=CC=CC=1)=[O:5])[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[NH:24][C:23](=[O:25])[CH2:22][CH2:21][N:9]2[C:10](=[O:20])[C:11]=1[OH:12])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 135970954HCID 135970954, compound

Product 1

HCID 135970953HCID 135970953, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Reaction of intermediate 10, 3-benzyloxy-4,8-dioxo-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidine-2-carboxylic acid ethyl ester, (0.543 g, 1.58 mmol) with trifluoroacetic acid (20 ml) as described in the preparation of intermediate 5 gave 0.296 g (74% yield) of the title ester as white crystals; mp 282° C. (dec) (ethyl acetate). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 1.26 (3H, t, J=7.1 Hz, CH3), 2.66 (2H, t, J=6.8 Hz, CH2), 4.13 (2H, t, J=6.8 Hz, CH2), 4.29 (2H, q, J=7.1 Hz, OCH2), 9.94 (1H, s, NH), 11.19 (1H, broad s, OH). HRMS (FAB POS) calculated for C10H12N3O5 [M+H+]: 254.077696. found: 254.078383.

Sources & evidence

ORD record
ord-da9d0e66ff5d4fa4bf239e9dd3a827b8
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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