Diisopropylethylamine → HCID 89561586, compound

HRID 510469Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=1.C(N(CC)C(C)C)(C)C.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:6]2[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=[C:2]([NH2:1])[N:7]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55° C. for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SO4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

Workup

customThe solvent was removed in vacuo
customthe residue was partitioned between DCM and water
extractionThe aqueous phase was extracted with further DCM
washthe combined organic fractions were washed with brine
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-50144f96d0134c90aa3a2851be357580
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096614B2

Reaction notes

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