Lawesson's reagent → 4-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 567757Notes

Reaction equation

HRID 567757 reaction equation
[NH2:1][C:2]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1COCC1>[Cl:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[NH:12][C:11]1[C:6]2[CH:5]=[C:4]([C:2](=[S:30])[NH2:1])[NH:20][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 212626756-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 212626564-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

144 mg (0.50 mmol) of 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine and 202 mg (0.5 mmol) of Lawesson's reagent in 5 ml of THF are heated to boiling for 17 h and the mixture is then evaporated. Column chromatography (SiO2, CH2Cl2/ethanol=15:1) of the residue and stirring in diethyl ether yields 4-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=9.8; TLC-Rf=0.44 (CH2Cl2/methanol=10:1); FAB-MS: (M+H)+=304; IR: (KBr) inter alia 1614s, 1566s, 1506m, 1474s, 1380m, 1354m, 1294m, 1134m.

Workup

  1. customthe mixture is then evaporated

Sources & evidence

ORD record
ord-c47eeb6273624ed1b16bb496c0a31cf5
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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