Ethanol → Cyclopropanesulphonic acid 4'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3'-methyl-biphenyl-2-yl ester

HRID 2416327Notes

Reaction equation

HRID 2416327 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:24][CH2:25][CH3:26])[C:13](I)=[C:14]([O:16][S:17]([CH:20]3[CH2:22][CH2:21]3)(=[O:19])=[O:18])[CH:15]=2)=[CH:4][N:3]=1.Br[C:28]1[CH:33]=[CH:32][C:31]([NH:34]C(=O)C(F)(F)F)=[C:30]([CH3:41])[CH:29]=1.C(O)C>O1CCOCC1.C(COC)OC>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([C:13]2[C:12]([O:24][CH2:25][CH3:26])=[CH:11][C:10]([CH2:9][C:5]3[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:15][C:14]=2[O:16][S:17]([CH:20]2[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:29][C:30]=1[CH3:41]

Participants

6

Reactant 3

HCID 702EthanolHCID 789606N-(4-bromo-2-methylphenyl)-2,2,2-trifluoroacetamideHCID 17937344HCID 17937344, compound

Product 1

HCID 17937299Cyclopropanesulphonic acid 4'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3'-methyl-biphenyl-2-yl esterYield 30%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Starting from cyclopropanesulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-iodo-phenyl ester (294 mg; 0.6 mmol) and N-(4-bromo-2-methyl-phenyl)-2,2,2-trifluoroacetamide (282 mg; 1.0 mmol) (first step in 12 ml dioxane instead of dimethylformamide with bis-triphenylphosphine-palladium dichloride (56 mg; 0.08 mmol) and second step in dimethoxyethane (8 ml) and ethanol (2 ml) with tetrakis-triphenylphosphine-palladium (69 mg; 0.06 mmol)), 151 mg (30%) cyclopropanesulphonic acid 4′-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3′-methyl-biphenyl-2-yl ester are obtained as a colourless powder.

Sources & evidence

ORD record
ord-396c24af6be44edc97bfe7d8d63937f9
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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