Diisopropylethylamine → N2-[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyrimidine-2,4-diamine

HRID 450380Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=2)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][N:3]=1.Cl.[F:22][C:23]1[CH:24]=[N:25][C:26]([C@@H:29]([NH2:31])[CH3:30])=[N:27][CH:28]=1.C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[N:25][C:26]([C@@H:29]([NH:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][N:3]=2)[CH3:30])=[N:27][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyrimidin-4-amine (Intermediate 30, 0.2 g) and [(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amine hydrochloride (Intermediate 15, 0.15 g) in n-BuOH (5 mL) with diisopropylethylamine (1 mL) was stirred at 70° C. for 4 hours. The resulting mixture was diluted with ethyl acetate (20 mL), and washed with brine (10 mL×3). The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to yield 0.2 g of title compound. MS (electrospray): 404 (M+1) for C16H18FN9O3.

Workup

washwashed with brine (10 mL×3)
customThe organic layer was dried
concentrationconcentrated
customThe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

Sources & evidence

ORD record: ord-56b663976e9048a18946e34c79d06c3a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486966B2

Reaction notes

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