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Methyl iodide → Butyl-ethyl-[6-methoxy-2,5,5-trimethyl-7-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-pyrrolo [2,3-d]pyrimidin-4-yl]-amine

HRID 1737667
Notes
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Reaction equation

HRID 1737667 reaction equation
[CH2:1]([N:5]([CH2:28][CH3:29])[C:6]1[C:7]2[C:15]([CH3:17])([CH3:16])[CH:14]([OH:18])[N:13]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH3:32]I>C1COCC1>[CH2:1]([N:5]([CH2:28][CH3:29])[C:6]1[C:7]2[C:15]([CH3:16])([CH3:17])[CH:14]([O:18][CH3:32])[N:13]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21912340HCID 21912340, compound

Product 1

HCID 21912372Butyl-ethyl-[6-methoxy-2,5,5-trimethyl-7-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-pyrrolo [2,3-d]pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(butyl-ethyl-amino)-2,5,5-trimethyl-7-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-6-ol] (20 mg, 0.05 mmol) in 1 ml of dry THF was treated with sodium hydride (60% in oil, 4 mg, 0.1 mmol) and then methyl iodide (0.3 ml) was added at room temperature. After stirring at room temperature for 2.5 hours, the mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 26 mg of crude material. After silica gel column purification with 10% ethyl acetate in hexane, 19 mg of a colorless oil of the title compound was obtained. 1H NMR (CDCl3) δ6.92 (s, 1H), 6.89 (s, 1H), 4.48 (s, 1H), 3.1-3.3 (m, 4H), 3.11 (s, 3H), 2.32 (s, 3H), 2.28 (s, 3H), 2.20 (s, 3H), 2.19 (s, 3H), 1.45 (s, 3H), 1.44 (s, 3H), 1.4-1.52 (m, 2H), 1.2-1.4 (m, 2H), 1.10 (t, 3H), 0.90 (t, 3H) ppm.

Workup

  1. customthe mixture was quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f3b03e54d39542b29b9e7bb16afc6ea9
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05962479

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes