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

HRID 536127Notes

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-eee527d80048474f9203538ca965df10
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859563B2

Reaction notes

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