Potassium Carbonate → HCID 178428544, compound

HRID 2389979Notes

Reaction equation

HRID 2389979 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 178511715HCID 178511715, compound

Product 1

HCID 178428544HCID 178428544, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-4-chloro-6-methylpyrimidine (1.18 g, 8.24 mmol), trans-4-aminocyclohexanol (1.00 g, 6.60 mmol), potassium carbonate (1.82 g, 13.2 mmol), and diisopropylethyl amine (1.44 mL, 8.24 mmol) in dimethylacetamide (20.0 mL) was heated at 160° C. in a sealed tube overnight. The reaction mixture was diluted with ethyl acetate, filtered, and the filtrate was concentrated. The residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-5%) to afford the title compound as a foamy solid (1.47 g, 99%).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with chloroform/7 N ammonia in methanol (0.5-5%)

Sources & evidence

ORD record
ord-d0b365315376411494fb147d595876f0
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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