Potassium Phosphate, Tribasic → 2-(2-Hydroxyphenyl)-9-(2-methoxyphenyl)purine-6-carboxamide

HRID 391643Notes

Reaction equation

HRID 391643 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([O:26]CC)=O)=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])=[N:6][C:7]=1[NH:8][C:9]1C=CC=CC=1OC.[NH2:29]C1C(C(OCC)=O)=NC(Cl)=NC=1NC1C=CC=CC=1OC.OC1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2[C:82]2[C:87]([O:88][CH3:89])=[CH:86][CH:85]=[CH:84][C:83]=2OC)CCCCC1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:5]1[N:6]=[C:7]2[C:2]([N:1]=[CH:9][N:8]2[C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][C:87]=2[O:88][CH3:89])=[C:3]([C:24]([NH2:29])=[O:26])[N:4]=1

Participants

10

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474575Ethyl 5-amino-2-chloro-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 136037538Ethyl 5-amino-2-(2-hydroxyphenyl)-6-[(2-methoxyphenyl)amino]pyrimidine-4-carboxylate

Product 1

HCID 1358672892-(2-Hydroxyphenyl)-9-(2-methoxyphenyl)purine-6-carboxamideYield 50%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-amino-2-(2-hydroxyphenyl)-6-[(2-methoxyphenyl)amino]pyrimidine-4-carboxylate. In a microwave flask was placed ethyl 5-amino-2-chloro-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (400 mg, 1.24 mmol), 3-hydroxyphenylboronic acid (260 mg, 1.86 mmol), potassium phosphate (531 mg, 2.504 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (77 mg, 0.188 mmol) and palladium (II) acetate (42.2 mg, 0.188 mmol) in tetrahydrofuran (20 mL) and water (2 mL) and the reaction mixture was heated at 120° C. for 60 min in the microwave. The reaction mixture was filtered and the crude product adsorbed onto silica gel. Flash chromatography (40% EtOAc in hexanes) afforded the title compound (235 mg, 0.62 mmol, 50%) as a tan solid. MS (ESI) m/z 381.3[M+1]+.

Workup

  1. customIn a microwave flask was placed
  2. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-cef5ecf7da314b9c9db27b1edaaabeac
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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