Acetonitrile → HCID 23633255, compound

HRID 254779Notes

Reaction equation

HRID 254779 reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[N:5]=[C:4]([NH2:20])[N:3]=1.[C:21]([O-:24])([O-])=[O:22].[Na+].[Na+].[CH3:27][C:28]#[N:29]>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>[NH2:29][C@@H:28]([CH2:27][C:10]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[C:6]([S:8][CH2:9][C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=3)[N:5]=[C:4]([NH2:20])[N:3]=2)=[CH:12][CH:11]=1)[C:21]([OH:24])=[O:22]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 86614308HCID 86614308, compound

Product 1

HCID 23633255HCID 23633255, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

4-Chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine (0.1 g, 0.331 mmol), L-p-boronophenylalanine (83 mg, 0.397 mmol), Pd(PPh3)2Cl2 (14 mg, 0.020 mmol), Na2CO3 (77 mg, 0.729 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 57 mg of the title compound. M+1=431; 1H NMR (CD3OD) δ 7.85 (s, 1H), 7.79 (d, 2H), 7.72 (d, 3H), 7.46 (dd, 1H), 7.35 (m, 4H), 6.95 (s, 1H), 4.58 (s, 2H), 4.17 (m, 1H), 3.26 (m, 1H), 3.11 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-13f71a394f8e48369e4fb9284d1c0d98
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

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