Triethylamine → HCID 58626065, compound

HRID 1161698Notes

Reaction equation

HRID 1161698 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.Cl.[NH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1.C(N(CC)CC)C>C(O)CCC>[Cl:1][C:2]1[N:7]=[C:6]([NH:16][CH:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([NH:16][CH:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2415542,4-Dichloro-6-phenylpyrimidineHCID 522619(1s,4s)-4-Aminocyclohexan-1-ol hydrochloride

Product 2

HCID 58626065HCID 58626065, compoundHCID 58626072HCID 58626072, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

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%).

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. additiondiluted with water (25 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customThe organic layers were collected
  5. washwashed with water (20 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe residue thus obtained
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0e9f53df33864f84b48267bb9f26c477
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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