Acetaldehyde → HCID 178464519, compound

HRID 1819416Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][C:27]([F:30])([F:29])[F:28])[N:11]=2)[CH2:4][CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)O[C:33]([CH3:35])=O.[Na+].C(=O)C.C([O-])(O)=O.[Na+]>CC(O)=O.CO>[CH2:33]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][C:27]([F:29])([F:30])[F:28])[N:11]=2)[CH2:6][CH2:7]1)[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

4-{[(trans-4-Aminocyclohexyl)methyl]amino}-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidine-5-carbonitrile (150 mg, 0.36 mmol) was dissolved in a solution of 1% AcOH in MeOH. The solution was cooled to 0° C. and to this cold solution were added NaBH(OAc)3 and acetaldehyde. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then treated with saturated NaHCO3 and extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using 9:1:0.1 CH2Cl2:MeOH:NH4OH as an eluent to afford 24 mg (15%) of the title compound, m/z 449.4 (M+1)+.

Workup

extractionextracted with EtOAc
dry with materialThe organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-adbffed48c4440f0946b436b45526f30
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601714B2

Reaction notes

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