Water → 6-acetyl-2-[4-(1,3-oxazol-5-yl)anilino]-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one

HRID 1930679Notes

Reaction equation

[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[NH:14])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.[C:16]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH:21]([C:26](OC)=[O:27])[CH2:20]1)(=[O:18])[CH3:17].[O-]CC.[Na+].O>C(O)C>[OH:27][C:26]1[C:21]2[CH2:20][N:19]([C:16](=[O:18])[CH3:17])[CH2:24][CH2:23][C:22]=2[N:14]=[C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)=[CH:11][CH:10]=2)[N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-(4-(Oxazol-5-yl)phenyl)guanidine (2 g, 9.89 mmol, example 1e), methyl 1-acetyl-4-oxopiperidine-3-carboxylate (1.970 g, 9.89 mmol) and sodium ethoxide (0.673 g, 9.89 mmol) in ethanol were charged in a thick wall glass which was sealed and heated at 100° C. under microwave irradiation. The reaction mixture was allowed to reach room temperature and water was added until a solid was obtained. The solid was filtered and dried in a vacuum oven at 40° C. overnight yielding 1-(4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (1.400 g, 40.3%).

Workup

customwas sealed
customto reach room temperature
customwas obtained
filtrationThe solid was filtered
customdried in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record: ord-07f8250ed1b64cd99bade80f095080a9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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