Lithium → HCID 89445519, compound

HRID 632729Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]#[N:16])[CH2:10][CH2:9]2)[C:3]=1[CH2:23][CH3:24].[Li]>C1COCC1>[NH2:16][CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][N:8]([C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[CH2:23][CH3:24])[CH2:9][CH2:10]1)[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of [4-(6-Amino-5-ethyl-pyrimidin-4-yl)-piperazin-1-yl]-cyclohexyl-acetonitrile (28.00 mg; 0.09 mmol; 1.00 eq.) in THF (4.00 ml; 49.37 mmol; 579.16 eq.), lithium 9-bbn hydride (0.38 ml; 0.38 mmol; 4.50 eq.) in THF was added, and the mixture stirred at 50° C. for four hours. LC-MS analysis indicated the reaction is incomplete, starting material still present. Add 0.1 ml more of lithium 9-bbn hydride solution and stir the reaction mixture overnight at 60° C. LC-MS analysis indicated the reaction was complete. The reaction mixture was filtered through a glass membrane syringe filter unit and evaporated to dryness. The residue was dissolved in DMSO (3 ml) and purified by reverse phase HPLC (Waters, basic buffer) to afford the title compound (13.9 mg; 0.04 mmol) as a white glass in 47.2% yield. LC-MS: (M+1=333.4, obsd.=333.3).

Workup

stirringstir the reaction mixture overnight at 60° C
filtrationThe reaction mixture was filtered through a glass membrane syringe
filtrationfilter unit
customevaporated to dryness
dissolutionThe residue was dissolved in DMSO (3 ml)
custompurified by reverse phase HPLC (Waters, basic buffer)

Sources & evidence

ORD record: ord-bf5080d655d94b69a0ffb330eff277bb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321760B2

Reaction notes

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