1,2-Dichloroethane → tert-butyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate

HRID 384266Notes

Reaction equation

HRID 384266 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]2[C:20]([C:21]([OH:23])=O)=[CH:19][N:18]=[C:17](Cl)[N:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]1[CH:30]=[C:29]2[N:31]=[N:32][N:33]([OH:34])[C:28]2=[CH:27][CH:26]=1.O.C(Cl)CCl.[NH4+:40].[OH-]>CN(C=O)C.CCOC(C)=O.O>[N:33]1([O:34][C:17]2[N:16]=[C:15]([NH:14][CH2:13][CH:10]3[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]3)[C:20]([C:21](=[O:23])[NH2:40])=[CH:19][N:18]=2)[C:28]2[CH:27]=[CH:26][CH:25]=[CH:30][C:29]=2[N:31]=[N:32]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 580989024-((1-(Tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylic acid

Product 1

HCID 66841163tert-butyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylateYield 73.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylic acid (503 mg, 1.41 mmol) and HOBt monohydrate (280 mg, 1.83 mmol) in DMF (8 mL), EDC (352 mg, 1.83 mmol) was added. After 1 h of stirring, conc. NH4OH (0.400 mL, ca. 5.60 mmol) was added. The mixture was stirred at room temperature for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate (472 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-140bd3dcc3cc41309db17aebdbfd78c0
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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