Piperidin-4-ol → 4-Benzylthio-5-methoxycarbonyl-6-(4-hydroxypiperidine-1-yl)-2-chloropyrimidine

HRID 917624

Reaction equation

HRID 917624 reaction equation
[CH2:1]([S:8][C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13](Cl)[N:12]=[C:11]([Cl:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(SC1C(C(OC)=O)=C(SCC2C=CC=CC=2)N=C(Cl)N=1)C1C=CC=CC=1.[OH:48][CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:1]([S:8][C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([N:52]2[CH2:53][CH2:54][CH:49]([OH:48])[CH2:50][CH2:51]2)[N:12]=[C:11]([Cl:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 79341Piperidin-4-ol2×HCID 178482644-Benzylthio-5-methoxycarbonyl-2,6-dichloropyrimidineHCID 178483164,6-Dibenzylthio-5-methoxycarbonyl-2-chloropyrimidine

Product 1

HCID 178482664-Benzylthio-5-methoxycarbonyl-6-(4-hydroxypiperidine-1-yl)-2-chloropyrimidine

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent2×

Procedure

A mixture of 4-benzylthio-5-methoxycarbonyl-2,6-dichloropyrimidine and 4,6-dibenzylthio-5-methoxycarbonyl-2-chloropyrimidine (prepared in the above (3)) 97 mg, 4-hydroxypiperidine 29 mg, triethylamine 29 mg and toluene 2.5 mg is stirred at room temperature for 4 hours. Further, 4-hydroxypiperidine 3 mg and triethylamine 3 mg are added thereto, and the mixture is stirred for 30 minutes. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-benzylthio-5-methoxycarbonyl-6-(4-hydroxypiperidine-1-yl)-2-chloropyrimidine as a colorless caramel, 120 mg.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df73e7eb66434dc5b166bdc75aa4b9c2
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Linked notes

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