Cesium carbonate → HCID 25013661, compound

HRID 2093477Notes

Reaction equation

[F:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:28]1[N:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=1>CN1C(=O)CCC1.C(OCC)(=O)C>[F:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:20][CH2:19][N:18]([C:28]4[N:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(5-fluoro-2-methylpyrimidin-4-yl)-4,4′-bipiperidine (16 mg, 0.058 mmol) and cesium carbonate (57 mg, 0.17 mmol) were stirred in NMP (0.6 ml) and 2-chloro-5-fluoropyrimidine (0.014 mL, 0.116 mmol) was added. The mixture was heated at 70° C. for 1 h. The reaction was cooled down to r.t. and diluted with ethyl acetate (5 mL) and was washed with water 2 mL (×1) and brine 2 mL (×1). The organic phase was dried over magnesium sulfate, filtered, and concentrated on rotavapor. The crude material was purified by preparative TLC with 30% acetone: hexane to yield the titled compound. LC-MS: 375.06 (M+H). Examples reported in Table 14 are prepared in accordance with Procedure 14.1.

Workup

temperatureThe reaction was cooled down to r.t.
washwas washed with water 2 mL (×1) and brine 2 mL (×1)
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated on rotavapor
customThe crude material was purified by preparative TLC with 30% acetone

Sources & evidence

ORD record: ord-264580d5f7404c2a984a0c61a3b5b4b1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445499B2

Reaction notes

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