Acetonitrile → HCID 23633254, compound

HRID 254778Notes

Reaction equation

HRID 254778 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([NH2:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-:20])([O-])=[O:18].[Na+].[Na+].[CH3:23][C:24]#[N:25]>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>[NH2:25][C@@H:24]([CH2:23][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:14]=[C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:10]=[C:11]([NH2:16])[N:12]=2)=[CH:4][CH:3]=1)[C:17]([OH:20])=[O:18]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 1488167HCID 1488167, compound

Product 1

HCID 23633254HCID 23633254, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

4-(Benzylthio)-6-chloropyrimidin-2-amine (0.1 g, 0.397 mmol), L-p-boronophenylalanine (0.1 g, 0.477 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (93 mg, 0.874 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 0.42 g of the title compound. M+1=381; 1H NMR (CD3OD) δ 7.8 (d, 2H), 7.37 (t, 4H), 7.23 (m, 2H), 7.16 (m, 1H), 6.98 (s, 1H), 4.43 (s, 2H), 4.20 (t, 1H), 3.29 (m, 1H), 3.13 (M, 1H).

Workup

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

Sources & evidence

ORD record
ord-bcf5145990304a7ebbc6f2c8e890d4e3
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

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