Acetonitrile → (2S)-2-Amino-3-(4-(2-amino-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid

HRID 559116Notes

Reaction equation

HRID 559116 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH2:22])[N:3]=1.[C:23]([O-:26])([O-])=[O:24].[Na+].[Na+].[CH3:29][C:30]#[N:31]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:31][C@@H:30]([CH2:29][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[C:6]([O:8][CH:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=3)[C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH2:22])[N:3]=2)=[CH:16][CH:15]=1)[C:23]([OH:26])=[O:24]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 866143094-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine

Product 1

HCID 23633256(2S)-2-Amino-3-(4-(2-amino-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

4-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine (0.14 g, 0.421 mmol), L-p-boronophenylalanine (110 mg, 0.505 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), Na2CO3 (98 mg, 0.926 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150° C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 74 mg of the title compound. M+1=469; 1H NMR (CD3OD) δ 7.83 (d, 2H), 7.47 (m, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 4.21 (t, 1H), 3.29 (m, 1H), 3.15 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified via prep HPLC

Sources & evidence

ORD record
ord-21a96d83c6544f9b850a0e052a2c3f71
Source dataset
uspto-grants-2011_11
Patent number
US08063057B2

Reaction notes

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