Sodium borohydride → 3-Hydroxymethyl-8-(2-methoxycarbonylamino-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine
Reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([NH:12][CH2:13][C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=3[NH:21][C:22]([O:24][CH3:25])=[O:23])[C:6]2=[N:5][C:4]=1[CH3:26])=[O:2].[BH4-].[Na+]>CO.Cl>[OH:2][CH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([NH:12][CH2:13][C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=3[NH:21][C:22]([O:24][CH3:25])=[O:23])[C:6]2=[N:5][C:4]=1[CH3:26]Participants
5
Procedure
2 g of 3-formyl-8-(2-methoxycarbonylamino-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine are suspended in 30 ml of methanol at RT, 0.2 g of sodium borohydride is added in portions, and the mixture is stirred at RT for 1 h. Subsequently, half the solvent is stripped off in vacuo, the residue is poured into ice-water, and the mixture is neutralized with a few drops of dilute hydrochloric acid and extracted four times with ethyl acetate. The collected organic phases are washed with water and dried over sodium sulfate. The solvent is stripped off in vacuo. The remaining yellowish residue completely crystallizes after some time. Recrystallization from ethyl acetate results in 1.3 g of the title compound of m.p. 170°-172° C.
Workup
- extractionextracted four times with ethyl acetate
- washThe collected organic phases are washed with water
- dry with materialdried over sodium sulfate
- customThe remaining yellowish residue completely crystallizes after some time
- customRecrystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-91151f26908c425383c869142beda47a
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665730
Reaction notes
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