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 1621970Notes

Reaction equation

HRID 1621970 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 NH4C1 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 NH4C1 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-6e816eb2b59740039acd95b36b2df7c4
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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