Potassium Phosphate, Tribasic → HCID 178513786, compound

HRID 391709Notes

Reaction equation

HRID 391709 reaction equation
[NH2:1][C:2]1[C:3]([C:30]([O:32]CC)=O)=[N:4][C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)=[N:6][C:7]=1[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15]C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.[NH2:35]C1C(C(OCC)=O)=NC(Cl)=NC=1N[C@H]1CC[C@H](NC(OC(C)(C)C)=O)CC1.[OH:63][C:64]1C=C(B(O)O)C=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([N:8]2[C:64](=[O:63])[NH:1][C:2]3[C:7]2=[N:6][C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)=[N:4][C:3]=3[C:30]([NH2:35])=[O:32])[CH2:10][CH2:11]1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 178470190HCID 178470190, compoundHCID 178470252HCID 178470252, compound

Product 1

HCID 178513786HCID 178513786, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-amino-6-(trans-4-(tert-butoxycarbonylamino)cyclohexylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate. Ethyl 5-amino-6-(trans-4-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloropyrimidine-4-carboxylate. (0.500 g, 1.21 mmol), 3-hydroxyphenylboronic acid (0.249 g, 1.81 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.075 g, 0.182 mmol), palladium acetate (0.041 g, 0.182 mmol) and potassium phosphate (0.52 g, 2.42 mmol) were combined in tetrahydrofuran (7 mL) and water (0.6 mL) and heated to 120° C. in a Biotage Emrys Optimizer microwave reactor for thirty min. The reaction solution was filtered and concentrated. The residue purified via Biotage chromatography (0 to 60% ethyl acetate in hexanes) to afford the title compound (0.150 g, 26%). MS (ESI) m/z 472[M+1]+.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated
  3. customThe residue purified via Biotage chromatography (0 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0c3cda815af642e984c29f7071eb5834
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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