Methyl iodide → HCID 59587980, compound

HRID 40740Notes

Reaction equation

HRID 40740 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:20]=3)[CH:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1.CI.[C:33]([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH3:33][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:26][CH2:27][O:28][CH2:29][CH2:30]5)[CH:20]=4)[CH:16]=[CH:15][N:14]=3)=[CH:10][CH:11]=2)=[N:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59588150N-(4-(2H-tetrazol-5-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine

Product 1

HCID 59587980HCID 59587980, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of N-(4-(2H-tetrazol-5-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine (0.20 g, 0.50 mmol), MeI (0.71 g, 5.0 mmol) and K2CO3 (0.35 g, 2.50 mmol) in acetone (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water, extracted with EtOAc (3×). The combined organic solution was dried over anhydrous MgSO4 and concentrated in vacuo to give a solid. Purification of this material by column chromatography on silica gel (40% EtOAc/hexane) provided N-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine as the major product. 1H NMR (DMSO-d6, 400 MHz) δ 10.00 (s, 1H), 8.60 (d, 1H), 8.05 (d, 2H), 8.00 (d, 2H), 7.78 (s, 1H), 7.65 (d, 1H), 7.50 (d, 1H), 7.42 (t, 1H), 7.18 (dd, 1H), 4.42 (s, 3H), 3.80 (m, 4H), 3.24 (m, 4H). MS (ESI) 415.13 (M+H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic solution was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a solid
  5. customPurification of this material by column chromatography on silica gel (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-c35c7ae5b5a542fbb0eb1e31235e600b
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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