Methyl iodide → HCID 70674573, compound

HRID 1747724Notes

Reaction equation

HRID 1747724 reaction equation
[CH:1]([OH:3])=[O:2].[NH2:4][C:5]1[C:10]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[C:9]([NH2:16])[N:8]=[C:7]([C:17]2[N:18]=[C:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[N:21]3)[N:6]=1.[CH3:34][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[CH:1]([OH:3])=[O:2].[NH2:4][C:5]1[C:10]([N:11]([CH3:34])[C:12](=[O:15])[CH2:13][CH3:14])=[C:9]([NH2:16])[N:8]=[C:7]([C:17]2[N:18]=[C:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[N:21]3)[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 70674461HCID 70674461, compound

Product 1

HCID 70674573HCID 70674573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

At 0° C., 50 mg (0.11 mmol) of N-{4,6-diamino-2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]pyrimidin-5-yl}propanamide formate were initially charged in THF (0.47 ml), and 22.3 mg of a 2 N solution of sodium bis(trimethylsilyl)amide in THF (0.12 mmol) were added. After 30 min at 0° C., 14 μl (0.22 mmol) of methyl iodide were added and the mixture was stirred at 20° C. for 20 hours. The mixture was then concentrated and the residue was purified by preparative HPLC (acetonitrile/water (+0.1% formic acid) gradient). This gave 17 mg of the target compound (32% of theory).

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was purified by preparative HPLC (acetonitrile/water (+0.1% formic acid) gradient)

Sources & evidence

ORD record
ord-269ce5f2f31541ef83accaca185f2e93
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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