Potassium Phosphate, Tribasic → HCID 24937986, compound

HRID 391624Notes

Reaction equation

HRID 391624 reaction equation
[NH2:1][C:2]1[C:3]([C:21](OCC)=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)=[N:6][C:7]=1[NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[NH2:26]C1C(C(OCC)=O)=NC(Cl)=NC=1NC1CCCC1.[OH:45][C:46]1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:9]1([N:8]2[C:46](=[O:45])[NH:1][C:2]3[C:7]2=[N:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)=[N:4][C:3]=3[C:21]([NH2:26])=[O:22])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474580HCID 57474580, compoundHCID 57474584HCID 57474584, compound

Product 1

HCID 24937986HCID 24937986, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-amino-6-(cyclopentylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate. In a microwave flask was placed ethyl 5-amino-2-chloro-6-(cyclopentylamino)pyrimidine-4-carboxylate (212 mg, 0.745 mmol), 3-hydroxyphenylboronic acid (154 mg, 1.12 mmol), potassium phosphate (316 mg, 1.49 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (45.8 mg, 0.112 mmol) and palladium (II) acetate (25.1 mg, 0.112 mmol) in tetrahydrofuran (3 mL) and water (0.3 mL) and the reaction mixture was heated at 120° C. for 30 min in the microwave. The reaction mixture was filtered and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (25-43% ethyl acetate in hexanes and a second chromatography using 0-2% methanol in methylene chloride) to provide the title compound (76.3 mg, 0.223 mmol, 30% yield). MS (ESI) m/z 343.2 [M+1]+.

Workup

  1. customIn a microwave flask was placed
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was purified by column chromatography (25-43% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bec74a3de2f245f4b348adadf82ad262
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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