Nitrogen → 8-Indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 12332

Reaction equation

HRID 12332 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:17][N:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[C:9]2[N:10]=[C:11]([S:14][CH3:15])[N:12]=[CH:13][C:8]=2[C:7]1=[O:27])=[O:5])[CH3:2].BrBr.N#N.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[C:8]2[CH:13]=[N:12][C:11]([S:14][CH3:15])=[N:10][C:9]=2[N:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[CH:17]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 24408BromineHCID 252228778-Indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 252228788-Indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.32 g, 0.84 mmol) in 5 mL of methylene chloride (CH2Cl2) was added bromine (43 μL, 0.84 mmol) slowly under N2. The solution was stirred at room temperature for 2 hours (or to completion). The solvent was removed under vacuum without heating. The residue was redissolved in 2 mL of CH2Cl2, and was added triethylamine (234 μL, 1.68 mmol) in 1 mL of CH2Cl2. The solution was stirred at rt for 4 hours. The progress of the reaction was monitored by LC-MS. The solvent was evaporated and the residue was applied onto a silica gel column. The product was eluted with EtOAc/hexanes (1:5-1:2.5, v/v) and obtained as a white solid (0.30 g, 94%). 1H NMR (300 MHz, CDCl3) δ (ppm): 9.42 (s, 1H), 8.59 (s, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.24 (s, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.40 (q, 2H), 3.00 (m, 4H), 2.35 (s, 3H), 2.10 (m, 2H), 1.40 (t, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. temperaturewithout heating
  3. dissolutionThe residue was redissolved in 2 mL of CH2Cl2
  4. stirringThe solution was stirred at rt for 4 hours
  5. customThe solvent was evaporated
  6. washThe product was eluted with EtOAc/hexanes (1:5-1:2.5

Sources & evidence

ORD record
ord-2321ae9f98384267a85d98e9a630843a
Source dataset
uspto-grants-2010_06
Patent number
US07728003B2

Linked notes

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