Hydrazine → 3-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid hydrazide

HRID 1097753Notes

Reaction equation

CO[C:3]([C:5]1[N:6]=[C:7]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:8]2[C:9](=[O:19])[C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[NH2:25][NH2:26]>CO>[CH2:12]([O:11][C:10]1[C:9](=[O:19])[N:8]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:7]2=[N:6][C:5]=1[C:3]([NH:25][NH2:26])=[O:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of the product from Example 8.1 (800 mg, 2.56 mmol) in methanol (30 mL), was added hydrazine (6.0 eq) at room temperature. The mixture was then heated at 45° C. for 4 h then partially concentrated in vacuo (not to dryness), then cooled to room temperature. The resulting solid was filtered, washed with water and dried under vacuum to afford the desired compound (650 mg, yield 78%).

Workup

concentrationthen partially concentrated in vacuo (not to dryness),
temperaturethen cooled to room temperature
filtrationThe resulting solid was filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-60d148ae5b604466b2b9f2b9de2d5058
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143268B2

Reaction notes

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