Hydrochloric Acid → HCID 44480270, compound

HRID 541563Notes

Reaction equation

HRID 541563 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:17][C:18]3[C:23]([Cl:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.Cl>COCCO.C(O)C>[Cl:24][C:23]1[CH:22]=[N:21][C:20]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:3]=3)[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]=1[N:19]=2)[CH:14]=[CH:15][CH:16]=3

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57962250HCID 57962250, compound

Product 1

HCID 44480270HCID 44480270, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
150 °C

Procedure

N-{3-[3-(3-Aminophenyl)propyl]phenyl}-2,5-dichloropyrimidin-4-amine (20 mg, 0.05 mmol) was stirred in 2-methoxyethanol (1.0 mL) and a solution of hydrogen chloride in ethanol (0.75 mL, 3.5 M). The mixture was heated to 150° C. for 30 minutes in a microwave. Purification by preparative LCMS gave the desired product (6.5 mg, 37%). LCMS for C19H18ClN4 (M+H)+: m/z=337.

Workup

  1. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-af7cf80ca8f94e9aa67f7909fccb3c39
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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