Triethylamine → 4-(1-Methyl-2-(2-methylprop-1-enyl)imidazol-5-yl)-2-anilinopyrimidine

HRID 2117760Notes

Reaction equation

HRID 2117760 reaction equation
CS(Cl)(=O)=O.[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH3:24])[C:22]([CH2:25][C:26]([CH3:29])(O)[CH3:27])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][N:23]1[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:18]=2)=[CH:20][N:21]=[C:22]1[CH:25]=[C:26]([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69309142HCID 69309142, compound

Product 1

HCID 693092264-(1-Methyl-2-(2-methylprop-1-enyl)imidazol-5-yl)-2-anilinopyrimidineYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (151 μl, 1.96 mmol), was added to a solution of 2-anilino-4-(1-methyl-2-(2-methyl-2-hydroxypropyl)imidazol-5-yl)pyrimidine (Method 97; 600 mg, 1.86 mmol), and triethylamine (777 μl, 5.58 mmol), in DCM (10 ml), at ambient temperature under nitrogen. The mixture was stirred for 3 hours then adsorbed directly onto silica gel and purified by chromatography eluting with EtOAc to give the title compound (235 mg, 42%). NMR: 1.98 (s, 3H), 2.14 (s, 3H), 3.99 (s, 3H), 6.24 (s, 1H), 6.98 (t, 1H), 7.10 (d, 1H), 7.28 (dd, 2H), 7.69-7.72 (m, 3H), 8.40 (d, 1H), 9.42 (s, 1H); m/z: 306.

Workup

  1. custompurified by chromatography
  2. washeluting with EtOAc

Sources & evidence

ORD record
ord-6af14f7263dc4c5bbea3a48d85db533c
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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