Diisopropylethylamine → N-[(4-fluorophenyl)methyl]-3-hydroxy-9-(methylamino)-4-oxo-pyrido[1,2-a]pyrimidine-2-carboxamide

HRID 547380Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:21]([NH:22][CH3:23])[CH2:20][CH2:19][CH2:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C>CC1C=CC=CC=1C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([NH:22][CH3:23])=[CH:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 156 °C

Procedure

To a solution of N-(4-fluorobenzyl)-3-hydroxy-9-(methylamino)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxamide hydrotrifluoroacetate and diisopropylethylamine (4 eqs.) in o-xylene was added Pd(C) (10%). The suspension was stirred and heated to 156° C. for 7 hours. The suspension was left cooling to room temperature and the catalyst was filtered off. The catalyst was washed with methanol and dichloromethane and the filtrate and catalyst washes were combined and the combined organic solutions were concentrated to dryness. The product was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: C18). After lyophilization of the pooled product fractions the product was obtained as bright yellow fluffy material.

Workup

waitThe suspension was left
temperaturecooling to room temperature
filtrationthe catalyst was filtered off
washThe catalyst was washed with methanol and dichloromethane
concentrationthe combined organic solutions were concentrated to dryness
customThe product was purified by preparative RP-HPLC
customAfter lyophilization of the pooled product fractions the product was obtained as bright yellow fluffy material

Sources & evidence

ORD record: ord-3b5b6a48ae244120bea923df66926ce7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939537B2

Reaction notes

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