Sodium Hydroxide → 1-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidine-4-carboxylic acid

HRID 41484Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:21]3[CH:20]=[N:19][C:18]([NH:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])=[N:17][C:16]=3[CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C1COCC1>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][C:18]1[N:19]=[CH:20][C:21]2[C:12]([N:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidine-4-carboxylic acid ethyl ester 13 (583 mg, 1.37 mmol) was dissolved in THF (10 mL), 2 N NaOH solution (5 mL) were added and the mixture was stirred for 3 h at 50° C. The mixture was evaporated to dryness, water was added and the pH was adjusted to 7 adding 2 N HCl solution. The aqueous layer was extracted twice with ethyl acetate and DCM. The combined organic layers were dried over sodium sulfate, filtered and evaporated to dryness. The obtained colorless solid (447 mg, 1.12 mmol, 82%) was used without further purification.

Workup

customThe mixture was evaporated to dryness, water
additionwas added
extractionThe aqueous layer was extracted twice with ethyl acetate and DCM
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-2f9120211bca48e0bdf05f4ce8ff6590
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530650B2

Reaction notes

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