Diisopropylethylamine → HCID 66589226, compound

HRID 1092215Notes

Reaction equation

HRID 1092215 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([N+:17]([O-:19])=[O:18])=[C:4]([CH3:20])[N:3]=1.CCN(C(C)C)C(C)C.[NH2:30][C@H:31]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[CH2:32][OH:33]>CCCCO>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[C:5]([N+:17]([O-:19])=[O:18])=[C:4]([CH3:20])[N:3]=[C:2]([NH:30][C@H:31]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[CH2:32][OH:33])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanolHCID 866217652-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 66589226HCID 66589226, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-5-nitropyrimidin-4-amine (Method 75; 1.0 g, 3.4 mmol), DIEA (0.57 g, 4.4 mmol), and (R)-2-amino-2-(4-fluorophenyl)ethanol (0.58 g, 3.7 mmol) in n-BuOH (15 ml) was heated to 60° C. for 2 hours. The reaction was then cooled to 25° C., concentrated, and treated with hexane. The resulting solid was collected by filtration to give the title compound (1.3 g, 93%). MS: Calcd.: 413; Found: [M+H]+ 414.

Workup

  1. concentrationconcentrated
  2. additiontreated with hexane
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-bb9368c75c0e41079420435559a39167
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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