Triethylamine → HCID 178525124, compound

HRID 1507505Notes

Reaction equation

HRID 1507505 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([OH:23])=[N:12][C:13]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:14][C:15]=1[Cl:16].C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15]([Cl:16])=[N:14][C:13]([CH:17]2[CH2:18][CH2:19][N:20]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH2:21][CH2:22]2)=[N:12][C:11]=1[OH:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 178517540HCID 178517540, compound

Product 1

HCID 178525124HCID 178525124, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a mixture of 5-(1,3-benzothiazol-2-yl)-6-chloro-2-(piperidin-4-yl)pyrimidin-4-ol (50 g, 144.16 mmol, 1.00 equiv) and triethylamine (36.5 g, 361.39 mmol, 2.51 equiv) in dichloromethane (300 ml) was added benzyl chloroformate (29.5 g, 172.93 mmol, 1.20 equiv) dropwise. The resulting solution was stirred overnight at room temperature. Upon concentrated under vacuum, the residue was purified by flash chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (2:1) to give 3 g of benzyl 4-[5-(1,3-benzothiazol-2-yl)-4-chloro-6-hydroxypyrimidin-2-yl]piperidine-1-carboxylate as yellow solid. MS m/z [M+H]+ (ESI): 481.

Workup

  1. concentrationUpon concentrated under vacuum
  2. customthe residue was purified by flash chromatography on a silica gel column
  3. washeluting with petroleum ether/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-3d735063560242fc9c3249526c715358
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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