Ethyl 2-chloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylate → Ethyl 2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylate

HRID 450387Notes

Reaction equation

HRID 450387 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][C:6]([C@@H:9]([NH2:11])[CH3:10])=[N:7][CH:8]=1.Cl[C:13]1[N:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]([N+:24]([O-:26])=[O:25])=[C:15]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[N:14]=1>>[F:2][C:3]1[CH:4]=[N:5][C:6]([C@@H:9]([NH:11][C:13]2[N:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]([N+:24]([O-:26])=[O:25])=[C:15]([NH:27][C:28]3[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=3)[N:14]=2)[CH3:10])=[N:7][CH:8]=1

Participants

3

Reactant 2

HCID 57757807Ethyl 2-chloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylate2×HCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochloride2×

Product 1

HCID 68781144Ethyl 2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylate

Procedure

The title compound was prepared using a procedure similar to the one described for the synthesis of Intermediate 18 using [(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amine hydrochloride (Intermediate 15) and ethyl 2-chloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylate (Intermediate 48) as the starting materials. LCMS: 432 [M+1].

Sources & evidence

ORD record
ord-9af269a995a345f3ab22897e33f2fef9
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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