Sodium Carbonate → Tetrahydrofuran-2-yl-methanesulphonic acid 3'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-yl ester

HRID 2416337Notes

Reaction equation

HRID 2416337 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:22][CH2:23][CH3:24])[C:13](I)=[C:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=2)=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:27]=[C:28]([B])[CH:29]=[CH:30][CH:31]=1.[C:33](=O)([O-])[O-].[Na+].[Na+].[CH2:39]([CH2:42][O:43][CH3:44])OC.C(O)C>>[NH2:25][C:26]1[CH:27]=[C:28]([C:13]2[C:12]([O:22][CH2:23][CH3:24])=[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]([CH2:20][CH:44]2[CH2:33][CH2:39][CH2:42][O:43]2)(=[O:19])=[O:18])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 20074477Dimethoxyethane ethanolHCID 201616813-Aminophenyl-boronHCID 86759564Methanesulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-iodo-phenyl ester

Product 1

HCID 17937295Tetrahydrofuran-2-yl-methanesulphonic acid 3'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-yl ester

Procedure

Starting from tetrahydrofuran-2-yl)-methanesulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-iodo-phenyl ester (220 mg; 0.5 mmol), 3-aminophenyl-boron acid (98 mg; 0.63 mmol), tetrakis-triphenylphosphine-palladium (29 mg; 0.03 mmol) and aqueous 2 M sodium carbonate solution (3.2 ml; 6.4 mmol) in a 4/1 dimethoxyethane/ethanol mixture (10 ml) (52%) tetrahydrofuran-2-yl-methanesulphonic acid 3′-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-yl ester are obtained as a yellow foam.

Workup

  1. customare obtained as a yellow foam

Sources & evidence

ORD record
ord-623462ccb5e441679a2f9f0ce0a8f5d6
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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