Triethylamine → HCID 22160572, compound

HRID 1089250Notes

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.[CH2:15]([O:22][CH2:23][CH:24]([CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:25][O:26][NH2:27])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[CH2:30]([O:29][CH2:28][CH:24]([CH2:23][O:22][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:25][O:26][NH:27][C:2]1[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=[C:6]([Cl:11])[C:7]=1[NH:8][CH:9]=[O:10])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (from Description 1a) (3.3 g, 14.0 mmol), 3-benzyloxy-2-benzyloxymethylprop-1-oxyamine (4.2 g, 14.0 mmol), triethylamine (5.8 ml, 41.6 mmol) and dioxan (100 ml) was stirred at 100° C. for 2.5 hours. The cooled reaction mixture was filtered and the precipitate collected and washed with dioxan (2×25 ml). The filtrate and washings were combined and evaporated to a syrup. Column chromatography on silica gel (eluted with chloroform-ethanol, 50:1) afforded the title compound (4.9 g, 70%). IR: υmax (KBr) 3240, 2910, 2860, 1690, 1585, 1565, 1475, 1420 cm-1. 1H NMR: δH [(CD3)2SO] 2.29 (1H, quintet, J=6.0, 5.6 Hz, CH), 3.56 (4H, d, J=5.6 Hz, 2×CH2OCH2Ph), 3.94 (2H, d, J=6.0 Hz, CH2ON) 4.46 (4H, s, 2×CH2Ph), 7.30 (10H, m, 2 ×Ph), 9.28 (1H, br.s, NCHO), 9.42 (1H, br.s, NCHO), 10.86 (2H, br.s, D2O exchangeable, 2×NHCHO).

Workup

customThe cooled reaction mixture
filtrationwas filtered
customthe precipitate collected
washwashed with dioxan (2×25 ml)
customevaporated to a syrup

Sources & evidence

ORD record: ord-8229c3be2bd346fd8dbfc6b5db6623e8
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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