4,6-Dichloro-5-methoxypyrimidine → HCID 25070327, compound

HRID 1927149Notes

Reaction equation

HRID 1927149 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH2:19])=[CH:7]2.CCN(C(C)C)C(C)C.[Cl:29][C:30]1[C:35]([O:36][CH3:37])=[C:34](Cl)[N:33]=[CH:32][N:31]=1>C(O)CCC>[Cl:29][C:30]1[N:31]=[CH:32][N:33]=[C:34]([NH:19][CH2:18][C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[C:35]=1[O:36][CH3:37]

Participants

5

Reactant 3

HCID 787204,6-Dichloro-5-methoxypyrimidineHCID 81531DiisopropylethylamineHCID 59264636HCID 59264636, compound

Product 1

HCID 25070327HCID 25070327, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of (8-chloro-2-phenylquinolin-3-yl)methanamine (0.035 g, 0.13 mmol) in n-butanol (3 mL) was treated with DIEA (0.046 mL, 0.26 mmol, 2.0 eq) followed with 4,6-dichloro-5-methoxypyrimidine (0.025 g, 0.14 mmol, 1 eq) at 100° C. for 8 h. The reaction mixture was concentrated and purified by column chromatography on a Redi-Sep™ column using 0 to 100% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 as eluent to provide 6-chloro-N-((8-chloro-2-phenylquinolin-3-yl)methyl)-5-methoxypyrimidin-4-amine as a white solid. 1H-NMR (DMSO-d6) δ ppm 8.33 (s, 1H), 8.20 (t, 1H), 8.02-8.04 (m, 1H), 7.99 (s, 1H), 7.93-7.95 (m, 1H), 7.70 (d, J=6.60, 1H), 7.46-7.61 (m, 1H), 4.73 (d, J=5.71, 2H), 2.51 (s, 3H), Mass Spectrum (ESI) m/e=412 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography on a Redi-Sep™ column

Sources & evidence

ORD record
ord-79e40d17bf42466abef4632a86945c26
Source dataset
uspto-grants-2012_05
Patent number
US08183258B2

Reaction notes

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