Potassium Carbonate → HCID 90310789, compound

HRID 1519159Notes

Reaction equation

HRID 1519159 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]([F:19])=[C:10]([OH:18])[C:11]([CH:14]3[CH2:17][CH2:16][CH2:15]3)=[CH:12][CH:13]=2)=[N:6][CH:7]=1.Cl[C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH2:28])[N:22]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]([F:19])=[C:10]([C:11]([CH:14]3[CH2:15][CH2:16][CH2:17]3)=[CH:12][CH:13]=2)[O:18][C:21]2[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH2:28])[N:22]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 2855718-Crown-6HCID 90311095HCID 90311095, compound

Product 1

HCID 90310789HCID 90310789, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (50 mg, 0.19 mmol), 4-chloro-6-methylpyrimidin-2-amine (30 mg, 0.20 mmol), K2CO3 (53 mg, 0.39 mmol), and 18-crown-6 (3 mg, 0.01 mmol) in DMSO (2 mL) was heated for 16 hours at 140° Celsius. The reaction was then cooled to room temperature, filtered, and the filtrate directly subjected to HPLC purification to give 4-[3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenoxy]-6-methylpyrimidin-2-amine (12 mg, 16%). MS (ESI): mass calcd. for C19H19FN6O, 366.16; m/z found, 367.3 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.27-8.22 (m, 1H), 8.11 (d, J=1.5, 1H), 7.78 (m, 1H), 7.29 (d, J=8.3, 1H), 6.67 (d, J=0.8, 1H), 3.68-3.55 (m, 1H), 2.51 (d, J=0.7, 3H), 2.31-2.13 (m, 4H), 2.11-1.98 (m, 1H), 1.91-1.81 (m, 1H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate directly subjected to HPLC purification

Sources & evidence

ORD record
ord-ccb2b7f8fce64cc3aae669eb2f42d638
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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