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

HRID 41483Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:15](Cl)=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])[CH3:22].N.O>C1COCC1>[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([C:15]2[C:9]3[CH:8]=[N:7][C:6]([NH:5][CH2:4][C:3]4[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=4[Cl:1])=[N:11][C:10]=3[CH:12]=[CH:13][N:14]=2)[CH2:28][CH2:27]1)=[O:25])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

(2-Chloro-benzyl)-(5-chloro-pyrido[4,3-d]pyrimidin-2-yl)-amine 9 (500 mg, 1.64 mmol), Piperidine-4-carboxylic acid ethyl ester 12 (0.51 mL, 3.28 mmol) and NH3 (25% solution in water, 0.22 mL, 3.28 mmol) were dissolved in THF (5 mL) and stirred at 100° C. in a high pressure flask for 15 hours. To the mixture water (5 mL) was added and the precipitate formed was filtered off and dried in vacuo. The obtained colorless solid (583 mg, 1.37 mmol, 84%) was used without further purification.

Workup

customthe precipitate formed
filtrationwas filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-1172c2765278437091facd59836387e8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530650B2

Reaction notes

Loading…