Cl.[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH:14]=O.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:12]=2[O:11][CH3:10])[S:7][CH:8]=1The HCl salt of 4-(chloromethyl)thiazol-2-amine (10 mmol) was suspended in DCM (50 ml), and 2,4-dimethoxybenzaldehyde (1.0 eq. of) and DIEA (1.0 eq.) were added. To the mixture, acetic acid (1 ml) was added followed by addition of sodium triacetoxyborohydride (2.5 eq.) and the reaction was stirred at room temperature overnight. The reaction mixture was filtered through Celite and washed with DCM. The filtrate was concentrated and purified by column chromatography using 0-10% gradient of 7 N ammonia/MeOH and DCM to give 4-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine.
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