Dimethylformamide → HCID 67200057, compound

HRID 1948742Notes

Reaction equation

HRID 1948742 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]=[C:7](C1C=CC=CC=1C)[C:6]([CH2:20]SC1N=CN=C3C=1NC=N3)=[CH:5]2.[NH2:31][C:32]1[N:37]=[C:36](Cl)[CH:35]=[C:34]([CH:39]([CH3:41])[CH3:40])[N:33]=1.[H-].[Na+].CN([CH:47]=[O:48])C>>[CH:39]([C:34]1[CH:35]=[C:36]([O:48][CH2:47][C:9]2[C:9]([C:10]3[CH:5]=[CH:4][CH:3]=[CH:2][CH:11]=3)=[N:8][C:7]3[C:11]([CH:10]=2)=[CH:2][CH:3]=[CH:4][C:6]=3[CH3:20])[N:37]=[C:32]([NH2:31])[N:33]=1)([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27736194-chloro-6-isopropylpyrimidin-2-amineHCID 67198236HCID 67198236, compound

Product 1

HCID 67200057HCID 67200057, compoundYield 30%

Conditions

Temperature
100 °C

Procedure

A mixture of Intermediate 6 (100 mg, 0.32 mmol), 2-amino-4-chloro-6-isopropylpyrimidine (58 mg, 0.38 mmol) and sodium hydride (60% in mineral oil, 18 mg, 0.45 mmol) in DMF (2 mL) was stirred at 100° C. for 45 minutes. Purification was by preparative HPLC (Method 1) followed by partitioning between DCM (20 mL) and 10% aqueous K2CO3 solution (10 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (37 mg, 30%). δH (CDCl3) 8.32 (s, 1H), 7.71-7.77 (m, 2H), 7.69 (d, J 8.1 Hz, 1H), 7.57 (d, J 9 Hz, 1H), 7.41-7.53 (m, 4H), 6.03 (s, 1H), 5.47 (s, 2H), 4.82 (br s, 2H), 2.83 (s, 3H), 2.64-2.79 (m, 1H), 1.21 (d, J 7 Hz, 6H). LCMS (ES+) 385.2 (M+H)+, RT 2.92 minutes (Method 3).

Workup

  1. customPurification
  2. customby partitioning between DCM (20 mL) and 10% aqueous K2CO3 solution (10 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cbb12c402af45b1b0abb02581bf53e1
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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