Bromine → 5-Bromo-6-chloro-2-[1-(3-isoquinolyl)ethylsulfanyl]pyrimidin-4-amine

HRID 1637753Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH:10]([C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:11])[N:3]=1.[Br:22]Br>CO>[NH2:1][C:2]1[C:7]([Br:22])=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH:10]([C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:11])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Amino-6-chloro-2-(1-(3-isoquinolyl)ethyl)thio-pyrimidine (475 mg, 1.5 mmole) is suspended in 15 ml methanol in a 50 ml one neck round bottom flask under nitrogen at 0° C. The suspension is treated slowly dropwise with bromine (85 μl, 1.65 mmole) and the reaction mixture is stirred 20 min at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×50 ml dichloromethane and 1×50 ml saturated sodium carbonate followed by 1×50 ml saturated sodium thiosulfate. The organic layer is dried over potassium carbonate and is concentrated in vacuo to a white foam. Crystallization from 1:9 diethyl ether/hexane afforded 513 mg (86%) of 4-Amino-5-bromo-6-chloro-2-(1-(3-isoquinolyl)ethyl)thio-pyrimidine as a white solid.

Workup

customThe volatiles are removed in vacuo
customthe residue is partitioned between 1×50 ml dichloromethane and 1×50 ml saturated sodium carbonate
dry with materialThe organic layer is dried over potassium carbonate
concentrationis concentrated in vacuo to a white foam
customCrystallization from 1:9 diethyl ether/hexane

Sources & evidence

ORD record: ord-d6b24bcf53b3457c8d9d9a4c2cf0f4ab
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043248

Reaction notes

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