Diisopropylethylamine → HCID 86659399, compound

HRID 2043444Notes

Reaction equation

HRID 2043444 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.Cl.[OH:20][CH2:21][C:22]1([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C>C(OCCO)C.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=[C:2]([N:25]2[CH2:26][CH2:27][C:22]([CH2:21][OH:20])([OH:28])[CH2:23][CH2:24]2)[CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 227444724-(Hydroxymethyl)-4-piperidinol hydrochlorideHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

Product 1

HCID 86659399HCID 86659399, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

150 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine and 97 mg of 4-(hydroxymethyl)piperidin-4-ol hydrochloride were dissolved in 3 ml of 2-ethoxyethanol, and 274 μl of N,N-diisopropylethylamine was added thereto, and the mixture was stirred at 135° C. for 20 hours. The reaction solution was air-cooled to room temperature, and then diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 194 mg of the objective compound as brown oil.

Workup

  1. temperatureThe reaction solution was air-cooled to room temperature
  2. washThe solution was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6a53b8b3e66042bf81f7f834a4fa0c41
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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