Acetonitrile → HCID 57818852, compound

HRID 705594Notes

Reaction equation

HRID 705594 reaction equation
[F:1][C:2]1[C:3]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH3:23])=[S:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[C:24](=O)([O-])[O-].[K+].[K+].[CH3:30][C:31]#N>O>[F:1][C:2]1[C:3]([NH:17][C:18](=[N:20][CH2:21][CH2:22][CH3:23])[S:19][CH2:24][CH2:31][CH3:30])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 57819041HCID 57819041, compound

Product 1

HCID 57818852HCID 57818852, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a magnetically stirred solution of 1-[5-Fluoro-2-(4-methyl-benzyloxy)-pyrimidin-4-yl]-3-propyl-thiourea (0.50 g, 1.40 mmol) in CH3CN (4 mL), was added potassium carbonate (0.20 g, 1.40 mmol) at room temperature and the mixture was stirred for 20 min. N-Propylbromide (0.19 g, 1.40 mmol) was added at room temperature and the resulting mixture stirred for 15 h. The reaction mixture was diluted with H2O and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and the solvent evaporated. The crude mixture was purified on silica (EtOAc/hexanes gradient) and evaporation of the product fractions gave 0.335 g (63%) of 1-[5-Fluoro-2-(4-methyl-benzyloxy)-pyrimidin-4-yl]-2,3-dipropyl-isothiourea as a pale yellow viscous liquid: 1H NMR (300 MHz, CDCl3) δ 10.56 (bs, 1H), 8.09 (d, J=2.6 Hz, 1H), 7.31 (m, 2H), 7.24 (m, 2H), 5.28 (s, 2H), 3.28 (dd, J=13.6, 6.5 Hz, 4H), 2.36 (s, 3H), 1.62 (m, 4H), 1.0 (t, J=7.4 Hz, 4H); HPLC-MS (ESI) m/z 377 (M+H)+.

Workup

  1. stirringthe resulting mixture stirred for 15 h
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe crude mixture was purified on silica (EtOAc/hexanes gradient) and evaporation of the product fractions

Sources & evidence

ORD record
ord-8e6bd82d96ca4521b17e509c1a4b4199
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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