Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4-Dichloro-6-phenylpyrimidine | HCID 241554 | — |
| Reactant | (1s,4s)-4-Aminocyclohexan-1-ol hydrochloride | HCID 522619 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 58626065 | HCID 58626065 | — |
| Product | HCID 58626072 | HCID 58626072 | — |
Reaction Steps
A mixture of compound 2,4-dichloro-6-phenyl-pyrimidine (0.5 g, 2.22 mmol), 4-aminocyclohexanol hydrochloride (0.12 g, 1.11 mmol), triethylamine (0.67 g, 6.62 mmol) in n-butanol (10 mL) was stirred at 120° C. for 12 hours under a nitrogen atmosphere. The reaction mixture was then concentrated under vacuum, diluted with water (25 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were collected, combined, washed with water (20 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to give the two compounds 4-(2-chloro-6-phenyl-pyrimidin-4-ylamino)-cyclohexanol and 4-(4-chloro-6-phenyl-pyrimidin-2-ylamino)-cyclohexanol in ratio 1:2 (overall yield: 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820654B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-0e9f53df33864f84b48267bb9f26c477 |
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| Source note | uspto-grants-2010_10 |
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