HCID 86647082, compound → 2-(5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-YL)propan-2-OL

HRID 1812378Notes

Reaction equation

HRID 1812378 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:10]=[C:11]([C:25](=[O:27])[CH3:26])[CH:12]=[N:13][C:14]=2[NH:15][C:16]2[CH:17]=[N:18][C:19]([Cl:24])=[C:20]([O:22][CH3:23])[CH:21]=2)[N:3]=1.[CH3:28][Mg]Br>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:10]=[C:11]([C:25]([OH:27])([CH3:28])[CH3:26])[CH:12]=[N:13][C:14]=2[NH:15][C:16]2[CH:17]=[N:18][C:19]([Cl:24])=[C:20]([O:22][CH3:23])[CH:21]=2)[N:3]=1

Participants

4

Reactant 2

HCID 86647082HCID 86647082, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 595484152-(5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-YL)propan-2-OLYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone (85 mg, 0.220 mmol) in 2 mL of THF at 0° C. was treated with methylmagnesium bromide (0.73 mL of 3.0 M solution in ether, 2.20 mmol) and stirred at this temperature for 15 min. It was quenched with ice cold saturated NH4Cl solution and extracted twice with EtOAc. The combined organic solution was concentrated and the residue was purified on a silica gel column and eluted with 50 to 100% EtOAc in DCM to give the title compound (23 mg, 26% yield) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.19 (br., 1H), 8.97 (d, J=2.6 Hz, 1H), 8.50 (d, J=2.6 Hz, 1H), 8.44 (d, J=2.3 Hz, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.95 (s, 1H), 7.80 (s, 1H), 5.21 (s, 1H), 3.94 (s, 3H), 2.47 (s, 3H), 1.49 (s, 6H). m/z (ESI, positive ion) 402.0 (M+H)+.

Workup

  1. customIt was quenched with ice cold saturated NH4Cl solution
  2. extractionextracted twice with EtOAc
  3. concentrationThe combined organic solution was concentrated
  4. customthe residue was purified on a silica gel column
  5. washeluted with 50 to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-02c403c626c9476c892299eaae5f962b
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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