Acetic Acid → HCID 68883960, compound

HRID 1723664Notes

Reaction equation

HRID 1723664 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][CH:14]3[CH2:16][CH2:15]3)[C:11]([CH3:17])=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:18][O:19][CH2:20][CH2:21][N:22]([C:33]([CH3:36])([CH3:35])[CH3:34])[S:23]([C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(O)(=O)C>O>[CH:14]1([CH2:13][N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:29]4[CH:28]=[CH:27][C:26]([S:23](=[O:24])(=[O:25])[N:22]([CH2:21][CH2:20][O:19][CH3:18])[C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:31][CH:30]=4)[N:7]=3)=[CH:9][N:10]=[C:11]2[CH3:17])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 68881545HCID 68881545, compoundHCID 68883909HCID 68883909, compound

Product 1

HCID 68883960HCID 68883960, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-(1-cyclopropylmethyl-2-methylimidazol-5-yl)pyrimidine (Method 54; 2 g, 8.73 mmol) was treated with N-(2-methoxyethyl)-N-(t-butyl)-4-iodobenzenesulphonamide (Method 77; 3.82 g, 9.61 mmol) under the conditions described in Example 22. The reaction was quenched by the addition of acetic acid (250 μl, 4.37 mmol), the mixture was poured into water and extracted with EtOAc. The extracts were combined, washed with water and then brine, dried and the solvent removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (97:3) to give the title compound (1.4 g, 32%) as a pale yellow foam. NMR: 0.01 (m, 2H) 0.18 (m, 2H) 1.90 (m, H) 2.26 (s, 3H) 3.15 (s, 3H) 3.37 (m, 4H) 4.42 (d, 2H) 7.08 (d, H) 7.52 (s, H) 7.58 (d, 2H) 7.75 (d, 2H) 8.30 (d, H) 9.75 (s, H); m/z 499.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water
  3. dry with materialbrine, dried
  4. customthe solvent removed by evaporation
  5. customThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (97:3)

Sources & evidence

ORD record
ord-6ffec68cf18f48649d1e4835c586ff15
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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