Cyclobutylamine → HCID 46192529, compound

HRID 1161650Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH:10]1([NH2:14])[CH2:13][CH2:12][CH2:11]1>CCN(C(C)C)C(C)C>[CH:10]1([NH:14][C:6]2[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 25 °C

Procedure

2,4,5-trichloro-pyrimidine (0.5 M in DMSO) cyclobutyl amine (0.5 M in DMSO, 160 μL) and DIEA (neat, 30 μL) were added to an 8-ml reaction vial. The vial was capped and the contents shaken at 25° C. for 22 h. The reaction mixture was concentrated in Genevac to provide 4-cyclobutylamino-2,5-dichloro-pyrimidine. The solid was treated with C16 (0.5 M in DMSO, 160 μL), concentrated in Genevac, and the resultant residue treated with EtOAc (160 ul). The vial was capped and the contents shaken at 75° C. for 22.5 hours. The reaction mixture was then concentrated in Genevac. The resultant crude product was dissolved in DMSO and purified by HPLC to provide 418 (11.9 mg, 35%). APCI LCMS: Retention time: 3.00 min (Method A), Observed mass: 419.99 [M+H].

Workup

customThe vial was capped
concentrationThe reaction mixture was concentrated in Genevac

Sources & evidence

ORD record: ord-287a4ed1c5ed461087753cc952e9078d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820648B2

Reaction notes

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