Water → ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6 (7H)yl)-5-pyrimidine carboxylate

HRID 2200910Notes

Reaction equation

HRID 2200910 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[CH2:8][NH:9][CH2:10][C:3]=12.[Cl:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:15][NH:16][C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=[C:19](S(C)=O)[N:18]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:15][NH:16][C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=[C:19]([N:9]2[CH2:8][C:4]3[C:3](=[N:2][CH:7]=[CH:6][CH:5]=3)[CH2:10]2)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 189536436,7-Dihydro-5H-pyrrolo[3,4-b]pyridine hydrochlorideHCID 22665570Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate

Product 1

HCID 118157304ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6 (7H)yl)-5-pyrimidine carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride salt (1.86 g, 12 mmol) was added into the solution of ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-methanesulfinyl-5-pyrimidine carboxylate in DCM. The mixture was cooled in an ice bath, and triethylamine was added dropwisely (2.5 mL, 17.9 mmol). The reaction mixture was stirred at ambient temperature overnight. LC-MS was used to monitor the reaction. After the completion of the reaction, water (30 mL) was added for precipitation. The solid was filtrated and dried to give ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridine-6(7H)yl)-5-pyrimidine carboxylate (3.0 g, 65.6% yield).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customthe reaction
  3. additionwas added for precipitation
  4. filtrationThe solid was filtrated
  5. customdried

Sources & evidence

ORD record
ord-917329570f6c4cc9a68c3e3dc6045897
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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