Sodium hydride → HCID 21934701, compound

HRID 1241392Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:17]1[S:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=1>C1COCC1>[N:1]1([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:17]3[S:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=3)[CH:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 45 °C

Procedure

6-Morpholin-4-yl-pyrimidin-4-ylamine (185 mg, 1.03 mmol) was stirred in 5 mL anhydrous THF under N2. Sodium hydride (82 mg, 60% dispersion, 2.05 mmol) was added and the reaction was warmed to 45° C. for 5 minutes. 2-chloro-thiazole-5-carbonitrile (208 mg, 1.44 mmol) was added and the reaction was heated to reflux. After 30 minutes added additional 2-chloro-thiazole-5-carbonitrile (85 mg, 0.59 mmol). After an additional 1 hour the reaction was cooled to room temperature, quenched with water and the THF was removed in vacuo. The mixture was neutralized with 1 M HCL and the resulting precipitate was filtered and washed with water. The solid was suspended in DMSO, filtered and washed with EtOAc to provide the title compound. 1H-NMR (400 MHz, CD3OD) 8.44 (1H, s), 7.95 (1H, s), 6.13 (1H, s), 3.81 (t, 4H, J=5.0 Hz), 3.63 (t, 4H, J=4.9 Hz). M+1=289.1.

Workup

temperaturethe reaction was heated to reflux
temperatureAfter an additional 1 hour the reaction was cooled to room temperature
customquenched with water
customthe THF was removed in vacuo
filtrationthe resulting precipitate was filtered
washwashed with water
filtrationfiltered
washwashed with EtOAc

Sources & evidence

ORD record: ord-f84cac260aa44079892b37f236487c5d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115597B2

Reaction notes

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