HCID 367509, compound → HCID 58032590, compound

HRID 2200929Notes

Reaction equation

[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[C:6]([NH2:10])[NH:7]2)=[N:3][CH:2]=1.[C:11]([C:13]1[CH:28]=[CH:27][C:16]([CH:17]=[C:18]([C:24](=O)[CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1)#[N:12].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:11]([C:13]1[CH:28]=[CH:27][C:16]([CH:17]2[N:7]3[C:6](=[N:5][C:4]4[N:3]=[CH:2][N:1]=[CH:9][C:8]=43)[NH:10][C:24]([CH3:25])=[C:18]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1)#[N:12]

Participants

Conditions

Temperature: 55 °C

Procedure

Under an atmosphere of argon, 7H-purine-8-amine (300 mg, 2.2 mmol) and ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (702 mg, 2.9 mmol, 1.3 eq.) were dissolved in DMF (5 ml), and solid sodium bicarbonate (932 mg, 11.1 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→90:10). After lyophilization of the appropriate fractions, the title compound was obtained as a solid (430 mg, 54% of theory). The isomeric compound (rac)-ethyl 9-(4-cyanophenyl)-7-methyl-6,9-dihydropyrimido[1,2-e]purine-8-carboxylate (see Example 23A) was obtained as a byproduct.

Workup

filtrationThe mixture was then filtered
distillationthe DMF from the filtrate was distilled off under reduced pressure
customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→90:10)

Sources & evidence

ORD record: ord-9b5dbd53ebc247f4914a58b98d07c58d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359362B2

Reaction notes

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