Acetonitrile → 4-Nitropyrimidin-2-amine

HRID 1363158Notes

Reaction equation

HRID 1363158 reaction equation
ClC1N=C(N[C@H]2C3C(=C(F)C=CC=3)OCC2)C([N+:20]([O-:22])=[O:21])=CN=1.ClC1[C:32](Cl)=[CH:31][C:27]2[N:28]=[CH:29][NH:30]C=2C=1.C(=O)([O-])[O-].[K+].[K+].C(#[N:42])C>CCOC(C)=O>[N+:20]([C:32]1[CH:31]=[CH:27][N:28]=[C:29]([NH2:30])[N:42]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 3317755,6-Dichloro-1H-benzimidazoleHCID 59704905(R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

Product 1

HCID 3322824-Nitropyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine in acetonitrile was treated with 5,6-dichlorobenzimidazole and potassium carbonate. The mixture was stirred at reflux for 6 hours, cooled to room temperature, diluted with 150 mL of EtOAc, and washed twice with 30 mL portions of water. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography (2% MeOH/DCM) gave the intermediate nitropyrimidinamine. The title compound was synthesized from the intermediate nitropyrimidinamine via the procedures described in Example 24. 1H-NMR (300 MHz, CDCl3) δ 8.7 (s, 1H), 8.3 (s, 1H), 8.2 (s, 1H), 7.8 (t, 1H), 7.0 (t, 1H), 6.6 (m, 2H), 5.9 (t, 1H), 4.6 (m, 1H), 4.4 (m, 1H), 3.0 (m, 1H), 2.3 (m, 1H).

Workup

  1. temperatureat reflux for 6 hours
  2. washwashed twice with 30 mL portions of water
  3. customThe organic layer was separated
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (2% MeOH/DCM)

Sources & evidence

ORD record
ord-a6a7a518fdc945e99cc3e56ce147cf1a
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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