Trifluoroacetic acid → 4-Amino-6-chloropyrimidine-2-thiol

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9]CC2C=CC(OC)=CC=2)[N:3]=1.FC(F)(F)C(O)=O>>[CH:7]1[C:2]([NH2:1])=[N:3][C:4](=[S:9])[NH:5][C:6]=1[Cl:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 470536HCID 470536, compound

Product 1

HCID 105153224-Amino-6-chloropyrimidine-2-thiol

Procedure

4-amino-6-chloro-2-(4-methoxyphenylmethylthio)-pyrimidine (11.0 g, 39.15 mmol: Cpd #93) and trifluoroacetic acid (84 ml) are heated to reflux for 20 hours, then the excess solvent is removed in vacuo. The sample is triturated with chloroform then stirred with ether and filtered. The solid is washed with ether then air dried, mp >320° C.

Workup

temperatureto reflux for 20 hours
customthe excess solvent is removed in vacuo
customThe sample is triturated with chloroform
filtrationfiltered
washThe solid is washed with ether
customair dried

Sources & evidence

ORD record: ord-c2af67178c6f4d18ae6b0358f21c0323
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981537

Reaction notes

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