Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 88053641, compound

HRID 2416341Notes

Reaction equation

HRID 2416341 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[C:12]([O:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:11]=2)=[CH:4][N:3]=1.[CH3:33][C:34]([O-:37])(C)C.[K+].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>CN(C)C=O>[C:34]([O:25][C:22]1[CH:21]=[CH:20][C:19]([C:13]2[C:14]([O:16][CH2:17][CH3:18])=[CH:15][C:10]([CH2:9][C:5]3[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:11][C:12]=2[O:26][S:27]([CH:30]([CH3:31])[CH3:32])(=[O:29])=[O:28])=[CH:24][CH:23]=1)(=[O:37])[CH3:33]

Participants

5

Reactant 3

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 17937305HCID 17937305, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 88053641HCID 88053641, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Starting from propane-2-sulphonic acid 4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-hydroxy-biphenyl-2-yl ester (example 15c) (137 mg; 0.30 mmol), potassium tert-butylate (42 mg; 0.37 mmol) and acetic anhydiide (0.028 ml; 0.30 mmol) in dimethylformamide (3.5 ml) at 0-5° C. (15 minutes) and then room temperature (3 hours), 39 mg (27%) 4′-(2,4-diamino-pyrimidin-5-ylmethyl)-6′-ethoxy-2′-(propane-2-sulphonyloxy)-biphenyl-4-yl acetate are obtained as a colourless powder.

Workup

  1. custom(15 minutes)

Sources & evidence

ORD record
ord-1a43445ec47d440e91fe2df0b2c598ac
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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