(S)-1-(1-Phenyl-1H-benzo[D]imidazol-2-YL)ethanamine → (S)-N4-(1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrimidine-4,6-diamine

HRID 243320Notes

Reaction equation

HRID 243320 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH2:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=1>O1CCOCC1>[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH:18][C:21]2[CH:22]=[C:23]([NH2:27])[N:24]=[CH:25][N:26]=2)[CH3:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 68157455(S)-1-(1-Phenyl-1H-benzo[D]imidazol-2-YL)ethanamineHCID 866688826-Chloropyrimidin-4-amine hydrochloride

Product 1

HCID 60161763(S)-N4-(1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrimidine-4,6-diamineYield 66.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (321.6 mg, 1.36 mmol, 1.00 equiv) in dioxane (10 mL) and 6-chloropyrimidin-4-amine hydrochloride (456.3 mg, 2.71 mmol, 2.00 equiv, 98%) was stirred overnight at 130° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a C18 column with acetonitrile/water (0-40%) to afford 298.6 mg (60%) of 146 hydrochloride as yellow crystals. LC-MS (ES, m/z): 331 [M+H]+H-NMR: (400 MHz, CD3OD, ppm) δ: 8.15 (s, 1H), 7.87-7.58 (m, 8H), 7.38-7.36 (m, 1H), 5.88 (br s, 1H), 5.41-5.36 (q, 1H), 1.747-1.73 (d, 3H)

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-aa372f928f6846d4bc816bd1374d26e7
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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