Sodium Hydroxide → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4,5,6-triamine

HRID 2174294Notes

Reaction equation

[F:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]2[N:20]=[C:19]([NH2:21])[C:18]([N:22]=NC3C=CC=CC=3)=[C:17]([NH2:30])[N:16]=2)=[N:6]1.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].CC#N.CO.C(Cl)Cl>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]2[N:20]=[C:19]([NH2:21])[C:18]([NH2:22])=[C:17]([NH2:30])[N:16]=2)=[N:6]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamine (Intermediate-7, 0.38 mmol) in DMF (2.5 mL) was added sodium hydroxide solution (2N, 3 equiv) and sodium dithionite (5.5 equiv). The reaction was heated to 150° C. and stirred for 2 h. The reaction mixture was diluted with CH2Cl2 and filtered. The filtrate was conc. and purified using SiO2 chromatography and an appropriate gradient (CH3CN/MeOH/CH2Cl2) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4,5,6-triamine as a tan solid (89% yield).

Workup

filtrationfiltered
custompurified

Sources & evidence

ORD record: ord-8b70105de56d47d89f5b1eab2c61bffe
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061030B2

Reaction notes

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