Methanol → HCID 57667050, compound

HRID 600857Notes

Reaction equation

HRID 600857 reaction equation
[NH2:1][C@@H:2]([CH2:5][N:6]([CH2:17][CH3:18])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:25]#[C:26]Br.CO>C1COCC1>[NH2:25][C:26]1[O:4][CH2:3][C@H:2]([CH2:5][N:6]([CH2:17][CH3:18])[C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=2)[N:1]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 67270826HCID 67270826, compound

Product 1

HCID 57667050HCID 57667050, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of (S)-2-amino-3-[ethyl-(2-trifluoromethyl-pyrimidin-4-yl)-amino]-propan-1-ol (0.185 g, 0.7 mmol) and K2CO3 (0.145 g, 1.05 mmol) in THF (5 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.111 g, 1.05 mmol) in THF (1 ml). The mixture was stirred for 2 hours, then methanol (1 ml) was added. The solution was evaporated over Isolute® Flash-NH2 silicagel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=95:5) yielded the title compound as light yellow oil, (0.084 g, 42%); MS (ISP): 290.0 ((M+H)+).

Workup

  1. customThe solution was evaporated over Isolute® Flash-NH2 silicagel

Sources & evidence

ORD record
ord-4a92d7a3dd9547bbbc4fe474d9d963bc
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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