Ethyl Acetate → HCID 71283978, compound

HRID 1752434Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:14][C:15](=[O:29])[C@@H:16]([NH:18][C:19]1[N:24]=[C:23](Cl)[N:22]=[C:21]([C:26]([NH2:28])=[O:27])[CH:20]=1)[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[NH2:14][C:15](=[O:29])[C@@H:16]([NH:18][C:19]1[N:24]=[C:23]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)[N:22]=[C:21]([C:26]([NH2:28])=[O:27])[CH:20]=1)[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(4-fluorophenyl)piperazine (112 mg, 0.62 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (150 mg, 0.62 mmol) and Cs2CO3 (235 mg, 0.62 mmol) in DMF (3.0 mL) was stirred at 100° C. for 14 hrs. The reaction was worked up with EtOAc and purified by silica gel flash chromatography (DCM/methanol) to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenyl)piperazin-1-yl)pyrimidine-4-carboxamide as a white solid (193 mg, 80%). 1H NMR (CD3OD): 6.90-7.1 (4H, m), 6.55 (1H, s), 4.3 (1H, m), 3.98 (4H, m), 3.10 (4H, m), 1.40 (3H, d, J=7.0 Hz). LC/MS: m/z=388 [M+H]+.

Workup

custompurified by silica gel flash chromatography (DCM/methanol)

Sources & evidence

ORD record: ord-669739a8ba534319b127548f2b0131e2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163008B2

Reaction notes

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