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-216679d7b3aa436191bed64e336747e4
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043248

Reaction notes

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