Triethylamine → 4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid

HRID 216032Notes

Reaction equation

HRID 216032 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:13][C:14]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)(C)C>[CH3:13][C:14]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18][N:17]([C:2]2[C:3]3[C:10]([CH3:11])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 510003794-Methylpiperidine-4-carboxylic acid hydrochloride

Product 1

HCID 670367814-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.274 g, 1.64 mmol) in isopropanol (10 mL) were added 4-methylpiperidine 4-carboxylic acid hydrochloric acid from step A (0.294 g, 1.64 mmol) and triethylamine (0.654 mL, 4.92 mmol). The reaction was heated to 180° C. for 1 hour under microwave conditions, concentrated, taken up with ice water, and neutralized to pH 3 with 6 N aq. HCl to precipitate the product. The product was collected by filtration and dried under vacuum overnight to give the title compound (0.42 g, 75%) as a gray solid. MS (ES+) [M+H]+=275.2.

Workup

  1. concentrationconcentrated
  2. customneutralized to pH 3 with 6 N aq. HCl to precipitate the product
  3. filtrationThe product was collected by filtration
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-19066ba6d4d64d8b95399f779f2e9401
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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