Methanol → HCID 10451274, compound

HRID 129010Notes

Reaction equation

HRID 129010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH2:19][O:20]C)[N:17]=[CH:18][C:13]=3[CH2:12][CH:11](C)[C:10]2=[O:23])=[CH:4][CH:3]=1.N1C=CC=C[CH:25]=1.I[Si](C)(C)C.CO>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH2:19][OH:20])[N:17]=[C:18]([CH3:25])[C:13]=3[CH2:12][CH2:11][C:10]2=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 85247Trimethylsilyl iodideHCID 19372996HCID 19372996, compound

Product 1

HCID 10451274HCID 10451274, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8-[(4-bromophenyl)methyl]-6-methyl-2-methoxymethyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (1.00 g, 2.70 mmol) and pyridine (0.11 g, 1.30 mmol) in CHCl3 (9 mL) was added iodotrimethylsilane (0.77 g, 3.80 mmol). The mixture was heated under reflux for 30 h and MeOH (0.5 mL) was added. The mixture was concentrated, taken up in CH2Cl2, washed with aqueous Na2SO3 and brine, dried (MgSO4), and concentrated. Purification by flash chromatography (5% MeOH/CH2Cl2) gave o.54 g (56%) of product as a colorless foam.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 h
  3. concentrationThe mixture was concentrated
  4. washwashed with aqueous Na2SO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (5% MeOH/CH2Cl2)
  8. customgave o

Sources & evidence

ORD record
ord-9ccbdeb3373942c78aa7c389f2f837e8
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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