Diisopropylethylamine → HCID 19808665, compound

HRID 373900Notes

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.[C:15]([O:18][CH2:19][CH:20]([CH2:31][O:32][NH2:33])[CH2:21][CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])(=[O:17])[CH3:16].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:33][O:32][CH2:31][CH:20]([CH2:19][O:18][C:15](=[O:17])[CH3:16])[CH2:21][CH2:22][P:23]([O:24][CH2:25][CH3:26])([O:27][CH2:28][CH3:29])=[O:30])[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4,6-Dichloro-2,5-diformamidopyrimidine (0.390 g, 1.66 mmol), diethyl 3-(acetoxymethyl)-4-(aminooxy)-butylphosphonate (0.380 g, 1.275 mmol) and N,N-diisopropylethylamine (0.58 ml, 3.22 mmol) were dissolved in diglyme (15 ml) and the resulting mixture was stirred at 100° C. for 3 hours. The reaction mixture was then allowed to cool, N,N-diisopropylethylamine hydrochloride was filtered off and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel (eluting with chloroform:ethanol 97:3) to give the title compound (0.480 g, 76%). 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, J=7Hz (OCH2CH3), 1.75 (4H, m, CH2CH2P), 2.01 (4H, m, COCH3, CHCH2) 4.0 (8H, m, CH2OAc, NOCH2, (OCH2)2) 8.15 (1H, s, 5-NHCHO), 9.25 (1H, s, 2-NHCHO), 9.40 (1H, br.s, D2O exchangeable, NHOCH2) 10.80 (2H, br.s. D2O exchangeable, 2x NHCHO). Found: C,41.97, H,5.80; N,13.17%. C17H27N5O8PCl requires: C,41.17; H,5.49; N,14.12%.

Workup

temperatureto cool
filtrationN,N-diisopropylethylamine hydrochloride was filtered off
customthe filtrate was evaporated to dryness
customThe residue was chromatographed on silica gel (eluting with chloroform:ethanol 97:3)

Sources & evidence

ORD record: ord-c3e5f0f5c1ee44868b915274cf133edd
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166198

Reaction notes

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