Hydrochloric Acid → HCID 18315671, compound

HRID 275939Notes

Reaction equation

C[O:2][CH2:3][C:4]1[N:9]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=[C:6]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]2[CH3:27])[C:5]=1[CH3:28].B(Br)(Br)Br.C(OCC)C.[ClH:38]>ClCCl.C(O)C>[ClH:38].[OH:2][CH2:3][C:4]1[N:9]=[C:8]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:7]=[C:6]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]2[CH3:27])[C:5]=1[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-methoxymethyl-5-methyl-2-phenylamino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(4.0 g, 9.7 mmol) in dichloromethane (50 ml) was cooled under 0° C. Boron tribromide (1M-dichloromethane solution, 38.8 ml, 38.8 mmol) was added dropwise to the solution. The reaction mixture was stirred for 30 minutes at 0° C. and poured into ice water. The separated dichloromethane layer was washed with aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, concentrated under a reduced pressure. Ethyl ether was added to the resulting residue to give a solid, which was then dissolved in ethanol and treated with ethyl ether saturated with hydrochloric acid to give 2.3 g of the titled compound.

Workup

washThe separated dichloromethane layer was washed with aqueous sodium bicarbonate solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure
additionEthyl ether was added to the resulting residue
customto give a solid, which

Sources & evidence

ORD record: ord-c5faf63056634f6bb868acc358faac27
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352993B1

Reaction notes

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