Trityl chloride → HCID 11432530, compound

HRID 552721Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@H:12]([OH:13])[C@H:14]([OH:15])[C@@H:16]([CH2:18][O:19][C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:17]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 6-chloro-9-β-D-ribofuranosylpurine (5.00 g, 17.4 mmol) and triphenylmethyl chloride (9.72 g, 34.8 mmol) in DMF (60 mL) was added DIPEA (2.7 mL, 19.1 mmol) dropwise. The reaction was heated to 40° C. overnight, cooled to r.t. and filtered. The yellow filtrate was diluted with chloroform and washed with water, 0.5 N HCl, and water. The organic layer was dried (Na2SO4), filtered and concentrated. The yellow foam was purified by flash chromatography (0 to 4% MeOH/CHCl3) to yield the product as a pale yellow foam (5.99 g, 65%).

Workup

temperaturecooled to r.t.
filtrationfiltered
additionThe yellow filtrate was diluted with chloroform
washwashed with water, 0.5 N HCl, and water
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe yellow foam was purified by flash chromatography (0 to 4% MeOH/CHCl3)

Sources & evidence

ORD record: ord-210b67e1e36f42fb8eea15c0f5e94e23
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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