2-Chloro-5-methylpyrimidin-4-amine → HCID 57675111, compound

HRID 1912185Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1>C(O)(=O)C>[NH2:8][C:6]1[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]3)=[CH:29][CH:30]=2)[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-chloro-5-methylpyrimidin-4-amine (540 mg, 3.7 mmol), tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (1.1 g, 3.7 mmol) was suspended in acetic acid (20 mL) and heated at 70° C. for 1 h. The mixture was allowed to cool to room temperature and acetic acid removed under reduced pressure. The residue was taken in water (20 mL) and neutralized to pH˜7. The resulting solution was extracted with EtOAc (30 mL) and the organic layer separated. The organic layer was washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 95%) as a yellow solid.

Workup

temperatureto cool to room temperature
customacetic acid removed under reduced pressure
extractionThe resulting solution was extracted with EtOAc (30 mL)
customthe organic layer separated
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-1b0d0420eca94f55ad5a7a7e8156dad7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604042B2

Reaction notes

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