2-Methoxyethylamine → 1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine

HRID 1398653Notes

Reaction equation

HRID 1398653 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13](C(Cl)(Cl)Cl)[N:12]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[N:20]=3)[C:11]=2[CH:26]=1>>[NH2:25][C:21]1[N:20]=[C:19]([N:12]2[C:11]3[CH:26]=[C:7]([Br:6])[CH:8]=[CH:9][C:10]=3[N:14]=[C:13]2[NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 681817331-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amineYield 45%

Procedure

A mixture of 2-methoxyethanamine (5 mL) and 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol) were stirred at RT for 3 days. The reaction mixture was then concentrated in vacuo and EtOAc/heptane (2:1) added. The solvent was removed in vacuo and this was repeated (×2). The resulting solid was then triturated from EtOAc:heptane (1:2). The solid was then dissolved in DCM (5 ml) and washed with water (2×2 ml). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (145 mg, 45% yield): 1H NMR (500 MHz, DMSO) delta 3.28 (3H, s), 3.71-3.53 (4H, m), 6.93 (1H, d, J=5.5), 7.14 (2H, s), 7.31-7.20 (2H, m), 7.67 (1H, d, J=1.6), 8.13 (1H, t, J=5.3), 8.41 (1H, d, J=5.5); LC-MS: m/z+363/365 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo and EtOAc/heptane (2:1)
  2. additionadded
  3. customThe solvent was removed in vacuo
  4. customThe resulting solid was then triturated from EtOAc:heptane (1:2)
  5. dissolutionThe solid was then dissolved in DCM (5 ml)
  6. washwashed with water (2×2 ml)
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b0d959f02564a62a05a4dea80ff169d
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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