Ethyl 7-benzyloxy-1,2-dimethyl-3,6-dioxo-2,3,4,6-tetrahydro-1h-pyrimido[2,1-c][1,2,4]triazine-8-carboxylate → HCID 54725630, compound

HRID 458689Notes

Reaction equation

HRID 458689 reaction equation
C([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([N:13]([CH3:22])[N:14]([CH3:21])[C:15](=[O:20])[CH2:16]2)=[N:11][C:10]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:22][N:13]1[C:12]2=[N:11][C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]([OH:8])[C:18](=[O:19])[N:17]2[CH2:16][C:15](=[O:20])[N:14]1[CH3:21]

Participants

6

Reactant 2

HCID 18442536Ethyl 7-benzyloxy-1,2-dimethyl-3,6-dioxo-2,3,4,6-tetrahydro-1h-pyrimido[2,1-c][1,2,4]triazine-8-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 54725630HCID 54725630, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution intermediate 21, ethyl 7-benzyloxy-1,2-dimethyl-3,6-dioxo-2,3,4,6-tetrahydro-1H-pyrimido[2,1-c][1,2,4]triazine-8-carboxylate, (0.306 g, 0.82 mmol) in a mixture of ethyl acetate (60 ml) and ethanol (60 ml),at 25° C., over 10% palladium on activated carbon (50 mg) and was treated with 1 atm of hydrogen for 1 h to give 0.226 g (97% yield) of the title amide as a white solid after recrystallization from ethyl acetate. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.47 (3H, t, J=7.1 Hz, CH3), 3.28 (3H, s, NCH3), 3.36 (3H, s, NCH3), 4.51 (2H, q, J=7.1 Hz, OCH2), 4.68 (2H, s, CH2), 10.60 (1H, s, OH). MS (ESI+) m/z 283 [M+H+].

Sources & evidence

ORD record
ord-f291394d06c042b09e5050c52c2dfacc
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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