tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate → 4-[4-(6-Oxo-1-phenyl-1,6-dihydropyridin-3-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 2375892Notes

Reaction equation

HRID 2375892 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:26]=[CH:27][C:28](=[O:37])[N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:30]=1>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:24][C:25]4[CH:26]=[CH:27][C:28](=[O:37])[N:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:30]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylateHCID 587098035-Amino-1-phenyl-1,2-dihydropyridin-2-one

Product 1

HCID 587098714-[4-(6-Oxo-1-phenyl-1,6-dihydropyridin-3-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (75 mg, 0.22 mmol) and 5-amino-1-phenyl-1H-pyridin-2-one (50 mg, 0.27 mmol) in 1-butanol (3 mL) was heated at 120° C. overnight, LC-MS showed the desired product together with some de-Boc product. After the mixture was cooled to rt, it was diluted with methylene chloride (3 mL), then N,N-diisopropylethylamine (0.1 mL, 0.6 mmol) and di-tert-butyldicarbonate (49 mg, 0.22 mmol) were added. The resulting mixture was stirred at rt for 30 min. The mixture was diluted with EtOAc (30 mL), then washed with brine (20 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized with EtOAc/Hexane to give the title compound as a green solid. LC-MS (ES, Pos.): 485 [MH+], and 1H NMR (DMSO-d6, 400 MHz): δ 1.43 (s, 9H), 2.50 (m, 2H), 3.56 (m, 2H), 4.04 (m, 2H), 6.39 (s, 1H), 6.56 (d, J=9.7 Hz, 1H), 6.66 (s, 1H), 7.39-7.57 (m, 5H), 7.81 (dd, J=9.7, 2.7 Hz, 1H), 8.17 (s, 1H), 8.34 (d, J=2.7 Hz, 1H), 9.17 (s, 1H), 11.94 (br s, 1H).

Sources & evidence

ORD record
ord-675f7e7aa5da42928e2fce3a5d5035ff
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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