Sodium ethoxide → HCID 178432899, compound

HRID 1930637Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[NH:15])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.O=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]1[C:31](OC)=[O:32].[O-]CC.[Na+]>C(O)C>[OH:32][C:31]1[C:19]2[CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23][C:18]=2[N:15]=[C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])=[CH:12][CH:11]=2)[N:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)guanidine (1.8 g, 8.36 mmol, example 9e), 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (2.151 g, 8.36 mmol) and sodium ethoxide (0.569 g, 8.36 mmol) in ethanol (10 mL) were charged in a thick glass vial, which was sealed and heated under microwave irradiation at 110° C. for 2 h. The reaction mixture was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and concentrated under reduced pressure yielding tert-butyl 4-hydroxy-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1.970 g, 55.8%). The product was used as such in the subsequent step. MS (ES+) m/z 423.3 (M+H)+

Workup

customwas sealed
customto reach room temperature
customthe solvent was evaporated under reduced pressure
dissolutionThe crude was dissolved in ethyl acetate
washwashed with water
customThe organic phase was dried under MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-50a96eb31267441f83367386a702be67
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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