Diisopropylethylamine → HCID 86649072, compound

HRID 1968535Notes

Reaction equation

HRID 1968535 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1.[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1.C(N(CC)C(C)C)(C)C>CC(O)C>[Cl:13][C:14]1[N:19]=[C:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2([OH:12])[CH2:11][CH2:10][CH2:9]2)[C:17]([Cl:21])=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 57031936HCID 57031936, compound

Product 1

HCID 86649072HCID 86649072, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

1-(2-Aminophenyl)cyclobutanol (56 mg, 0.343 mmol), 2,4,5-trichloropyrimidine (40 μl, 0.349 mmol) and N,N-diisopropylethylamine (120 μl, 0.694 mmol) were suspended in 2-propanol (1.5 mL) in a sealed tube, and the solution was heated to 85° C. for 4 hours. The reaction mixture was partitioned between H2O (15 mL) and CH2Cl2 (3×15 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (Analogix, 0 to 25% ethyl acetate-hexanes over 25 minutes, 4 g silica, 18 mL/minute) to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between H2O (15 mL) and CH2Cl2 (3×15 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography (Analogix, 0 to 25% ethyl acetate-hexanes over 25 minutes, 4 g silica, 18 mL/minute)

Sources & evidence

ORD record
ord-af3a3627f2904f5599f78be862805097
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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