Azetidine → HCID 67373871, compound

HRID 1678088Notes

Reaction equation

[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[CH:26]=[C:25]([CH3:27])[C:24](=S)[NH:23][C:22]3=[O:29])[CH2:13][CH2:12]2)[CH:8]=[C:7]([C:30]([F:33])([F:32])[F:31])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:34]1[CH2:37][CH2:36][CH2:35]1>C(O)C>[N:34]1([C:24]2[C:25]([CH3:27])=[CH:26][N:21]([CH2:20][CH2:19][CH2:18][CH2:17][N:14]3[CH2:15][CH2:16][N:11]([C:9]4[CH:8]=[C:7]([C:30]([F:33])([F:32])[F:31])[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:10]=4)[CH2:12][CH2:13]3)[C:22](=[O:29])[N:23]=2)[CH2:37][CH2:36][CH2:35]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-{4-[4-(2-tert-butyl-6-trifluoromethylpyrimidin-4-yl)piperazin-1-yl]butyl}-5-methyl-4-thioxo-3,4-dihydro-1H-pyrimidin-2-one from Example 2 (0.24 mmol, 0.12 g) and azetidine (5.81 mmol, 0.33 g) in ethanol (1.9 ml) was stirred at 60° C. in a microwave (Milestone Ethos 1600) for 1 hour. The reaction mixture was then concentrated and the resulting residue was purified by column chromatography on silica gel (eluent: CH2Cl2/methanol 95/5), resulting in 0.08 g of the title compound.

Workup

concentrationThe reaction mixture was then concentrated
customthe resulting residue was purified by column chromatography on silica gel (eluent: CH2Cl2/methanol 95/5)

Sources & evidence

ORD record: ord-b0bb361ee6754f2cb2ddc9669ac81520
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008488B2

Reaction notes

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