Sodium Hydroxide → 4-Chloro-6-(1H-5-indolyloxy)-2-pyrimidinamine

HRID 2264598Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[OH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2.[OH-].[Na+].CCOC(C)=O.CCCCCC>CC(C)=O.O>[NH2:1][C:2]1[N:3]=[C:4]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

10 g (61 mMol) 2-amino-4,6-dichloro-pyrimidine and 8.1 g (61 mMol) 5-hydroxyindole are suspended in 250 ml acetone. Then 120 ml 1 N NaOH in water are added and the mixture is stirred at an oilbath temperature of 70° C. for 2 h. The reaction mixture is partially concentrated and the residue diluted with water. Extraction with 3 portions of EtOAc, washing the organic layers twice with water and brine, drying (Na2SO4), addition of 100 g SiO2 and concentration in vacuo gives a powder. This is put on top of a chromatography column (SiO2; EtOAc/hexane 3:7) and eluted with EtOAc/hexane 3:7. Crystallization from hexane gives the title compound: m.p.: 192° C.; MS: [M+1]+=261; HPLC: AtRet=12.4.

Workup

concentrationThe reaction mixture is partially concentrated
additionthe residue diluted with water
extractionExtraction with 3 portions of EtOAc
washwashing the organic layers twice with water and brine
customdrying
addition(Na2SO4), addition of 100 g SiO2 and concentration in vacuo
customgives a powder
washeluted with EtOAc/hexane 3:7
customCrystallization from hexane

Sources & evidence

ORD record: ord-c5b770765eb7434e9e4b00bbbf28a74b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855215B2

Reaction notes

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