Diisopropylethylamine → HCID 19789722, compound

HRID 1655932Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (1.75 g, 7.4 mmol), 3-(methoxymethoxy)propoxyamine (1.0 g, 7.4 mmol) and N,N-diisopropylethylamine (2 g, 15.5 mmol) in dry diglyme was heated to 100° C. for 2 hr. The cooled reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate:hexane (50:50) then ethyl acetate to give the title compound as a yellow oil which was crystallised from ethyl acetate (1.2 g, 50%) mp 136°-8° C. νmax (KBr) 3240, 2920, 2880, 1705, 1640, 1590, 1565, 1495, 14650, 1410, and 1380 cm-1 ; δH [(CD3)2SO]1.85 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.24 (3H, s, OCH3), 3.58 (2H, t, J=6.3 Hz, CH2OCH2OCH3 ), 3.94 (2H, t, J=6.3 Hz, CH2ONH), 4.5 (2H, s, OCH2O), 8.15 (1H, s, NHCHO), 9.26 (1H, d, J=9.6 Hz, collapses to singlet on D2O, NHCHO), 9.4 (1H, s, D2O exchangeable NHOCH2), 10.73 (1H, s, D2O, exchangeable NHCHO), 10.84 (1H, d, J=9.6 Hz, D2O exchangeable, NHCHO).

Workup

customThe cooled reaction mixture
filtrationwas filtered
customthe filtrate was evaporated in vacuo
customThe residue was purified by column chromatography on silica eluting with ethyl acetate:hexane (50:50)

Sources & evidence

ORD record: ord-1d83b57e4eec4640b6c84bfdbd5c21ae
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252575

Reaction notes

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