Sodium ethoxide → tert-butyl 2-[4-(1,3-oxazol-5-yl)anilino]-4-oxo-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-carboxylate

HRID 1930535Notes

Reaction equation

[O-]CC.[Na+].O=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[C:19]([O:21]C)=O.[O:23]1[C:27]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[NH:36])=[CH:30][CH:29]=2)=[CH:26][N:25]=[CH:24]1>C(O)C>[OH:21][C:19]1[C:7]2[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11][C:6]=2[N:37]=[C:35]([NH:34][C:31]2[CH:32]=[CH:33][C:28]([C:27]3[O:23][CH:24]=[N:25][CH:26]=3)=[CH:29][CH:30]=2)[N:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium ethoxide (0.106 g, 1.55 mmol) was added to 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (0.400 g, 1.55 mmol, Example 3c) and 1-(4-(oxazol-5-yl)phenyl)guanidine (obtained from Example 1e, 0.314 g, 1.55 mmol) in ethanol (4 mL) and heated in a microwave reactor at 100° C. for 15 minutes. The suspension was diluted with ethanol (5 mL) and the precipitated product was filtered off and washed with cold ethanol to give tert-butyl 4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.480 g, 75%). No further purification. MS (ESI+)/(ESI−) M/Z 410/408

Workup

filtrationthe precipitated product was filtered off
washwashed with cold ethanol

Sources & evidence

ORD record: ord-67548acb8e714617949534fa3543f6a8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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