Diisopropylethylamine → HCID 66705963, compound

HRID 1916190Notes

Reaction equation

HRID 1916190 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH3:17])[N:5]=[CH:4][N:3]=1.[C:18]([O:22][C:23](=[O:32])[NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:21])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C>C(#N)C>[C:18]([O:22][C:23](=[O:32])[NH:24][CH2:25][CH:26]1[CH2:27][CH2:28][N:29]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[C:6]([CH3:17])[N:5]=[CH:4][N:3]=2)[CH2:30][CH2:31]1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 58072945HCID 58072945, compound

Product 1

HCID 66705963HCID 66705963, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The title compound is synthesized according to general procedure GP7 (method 2) starting from 2.0 g (8.17 mmol) 4-chloro-6-methyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine and 2.33 g (9.81 mmol) piperidin-4-ylmethyl-carbamic acid tert-butyl ester using 1.82 mL (10.6 mmoL) DIPEA in 50 mL ACN. The reaction mixture is stirred for 1 h at 80° C. The solvent is removed under reduced pressure. The residue is taken up in DCM/MeOH and filtered over silica. After removal of the solvent and extractive work up 3.1 g (90%) of the desired product is obtained. The product is used without further purification for the next step.

Workup

  1. customThe solvent is removed under reduced pressure
  2. filtrationfiltered over silica
  3. customAfter removal of the solvent and extractive work up 3.1 g (90%) of the desired product
  4. customis obtained
  5. customThe product is used without further purification for the next step

Sources & evidence

ORD record
ord-2bf5ed5ac297423995277b2956a949b9
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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