(4-prop-2-ynylcyclohexyl)methyl Acetate → [4-(3-{9[(4s,5s,2r,3r)-5-(n-Ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-6-aminopurin-2-yl}prop-2-ynyl)cyclohexyl]methyl acetate

HRID 430397Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:16][C@H:15]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[C@@H:14]([OH:22])[C@H:13]1[OH:23].[C:24]([O:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH:32]([CH2:35][C:36]#[CH:37])[CH2:31][CH2:30]1)(=[O:26])[CH3:25]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([O:27][CH2:28][CH:29]1[CH2:30][CH2:31][CH:32]([CH2:35][C:36]#[C:37][C:9]2[N:8]=[C:7]3[C:3]([N:4]=[CH:5][N:6]3[C@H:12]3[C@H:13]([OH:23])[C@H:14]([OH:22])[C@@H:15]([C:17](=[O:18])[NH:19][CH2:20][CH3:21])[O:16]3)=[C:2]([NH2:1])[N:10]=2)[CH2:33][CH2:34]1)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

To a degassed solution of 125 mg (0.29 mmol) of [(2S,3S,4R,5R)-5-(6amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-N-ethylcarboxamide (6.9), 150 mg (0.77 mmol) (5.6), and 1.0 mg CuI in 1.3 mL of TEA and 4 mL DMF was added 25 mg of Pd(PPh3)4. The solution was stirred for 72 h at 60° C. after which time the solution was filtered through celite and chromatographed on silica gel with MeOH-CHCl3 (5:95) to give JMR193 (10%).

Workup

filtrationwas filtered through celite
customchromatographed on silica gel with MeOH-CHCl3 (5:95)
customto give JMR193 (10%)

Sources & evidence

ORD record: ord-d4c38c6ea9b7459a93f4f0480a579d07
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06322771B1

Reaction notes

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