Water → HCID 68676970, compound

HRID 1989085Notes

Reaction equation

HRID 1989085 reaction equation
BrBr.[CH2:3]([O:5][C:6]([CH:8]1[CH2:19][N:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[C:9]1=[O:27])=[O:7])[CH3:4].C(N(CC)CC)C.O>C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[C:9](=[O:27])[C:10]2[CH:15]=[N:14][C:13]([S:16][CH3:17])=[N:12][C:11]=2[N:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24408BromineHCID 68677843HCID 68677843, compound

Product 1

HCID 68676970HCID 68676970, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.68 g, 4.3 mmol) was added to a solution of 8-benzyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1.53 g, 4.28 mmol) in DCM (20 mL). After 30 minutes, the reaction mixture was concentrated. The residue was redissolved in DCM (20 mL) and triethylamine (1.08 g, 10.7 mmol) was added. After 15 h, water (10 mL) was added, the organic layer separated, dried (MgSO4), and concentrated. Chromatography on silica (0-50% EtOAc/hexanes gradient) provided 0.39 g 8-benzyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.26 (s, 1H), 8.51 (s, 1H), 7.21-7.29 (m, 5H), 5.45 (s, 2H), 4.27 (q, 2H, J=7.1 Hz), 2.48 (s, 3H), 1.30 (t, 3H, J=7.1 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was redissolved in DCM (20 mL)
  3. waitAfter 15 h
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc10f676beba4cb793e4dbea68bd17c9
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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