Dichloromethane → 4-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

HRID 1398497Notes

Reaction equation

HRID 1398497 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][O:19][C:20]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][N:21]=1.C(Cl)Cl>C1COCC1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:26][C:25]2[C:20]([O:19][CH3:18])=[N:21][CH:22]=[CH:23][CH:24]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 27374883-Amino-2-methoxypyridine

Product 1

HCID 866695704-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-1,3,5-triazine (265.77 mg, 1.77 mmol) in THF (5 mL) was added DIPEA (0.266 mL, 1.61 mmol) followed by 2-methoxypyridin-3-amine (200 mg, 1.61 mmol). The resultant mixture was stirred at RT for 2 hr, then DCM was added and the organics washed with water (×2) and 0.5M aqueous HCl solution. Combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a beige solid: 1H NMR (250 MHz, DMSO) δ 3.88 (3H, s), 7.05 (1H, dd, J=7.54, 4.95 Hz), 7.86 (1H, dd, J=7.61, 1.68 Hz), 8.07 (1H, dd, J=4.95, 1.75 Hz), 8.56 (1H, s), 10.14 (1H, s); =+238.0/239.9 (M+H)+.

Workup

  1. washthe organics washed with water (×2) and 0.5M aqueous HCl solution
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a beige solid

Sources & evidence

ORD record
ord-119c8afef4a04627b132338977fbf4ab
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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