Water → HCID 11604271, compound

HRID 908519Notes

Reaction equation

[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH:33]=[CH:32][C:30](=[O:31])[NH:29][C:27]1=[O:28].O>N1C=CC=CC=1>[C:1]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH:33]=[CH:32][C:30](=[O:31])[NH:29][C:27]1=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Trityl chloride (0.358 g, 1.28 mmol) was added to a solution of 1-(4′-aminobutyl)uracil (contaminated by 11% 1,3-bis(4′-aminobutyl)uracil) (0.168 g) in anhydrous pyridine (15 mL). The reaction mixture was heated at 50° C. for 44 h, left to cool to room temperature, poured into cold water (50 mL) and extracted with DCM (3×25 mL). The organic extracts were washed with brine (40 mL), dried over Na2SO4 and concentrated in vacuo. Further purification was carried out by silica gel column chromatography, using Jones Chromatography Isolute SI columns with a gradient elution of 0→5% CH3OH in CHCl3. The fractions with Rf=0.51 (10% CH3OH/CHCl3) gave the title compound as a white crystalline solid (94 mg, ca 24%).

Workup

waitleft
temperatureto cool to room temperature
extractionextracted with DCM (3×25 mL)
washThe organic extracts were washed with brine (40 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customFurther purification
washwith a gradient elution of 0→5% CH3OH in CHCl3

Sources & evidence

ORD record: ord-c55777751d484be8968a5eb6a911e8bd
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017620B2

Reaction notes

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