Hydrochloric Acid → HCID 57818782, compound

HRID 705586Notes

Reaction equation

HRID 705586 reaction equation
[F:1][C:2]1[C:3]([NH2:17])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.CC([O-])(C)C.[K+].CC(O)(C)C.[N+:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[S:38]Cl)([O-:31])=[O:30].Cl>O>[F:1][C:2]1[C:3]([NH:17][S:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N+:29]([O-:31])=[O:30])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 243192-Nitrobenzenesulfenyl chlorideHCID 23665647Potassium tert-butoxideHCID 578185745-Fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-amine

Product 1

HCID 57818782HCID 57818782, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.05 g, 0.2 mmol) and a 1.0 M solution of KOtBu in tBuOH (1.0 mL, 1.0 mmol) was added nitrobenzene-sulfenyl chloride (0.044 g, 0.23 mmol) in one portion, and the resulting brown solution was stirred for 60 min. The reaction was diluted with water (2 mL) and neutralized to pH 7 with 1N HCl. The aq. phase was extracted with EtOAc (5 mL), and the organics were combined, dried over Na2SO4, filtered, and concentrated. The crude material was purified by reverse phase chromatography to yield the title compound (0.020 g, 26%) as a yellow solid: mp 184° C.; 1H NMR (300 MHz, CDCl3) δ 8.36 (d, J=7.25 Hz, 1H), 8.09 (d, J=2.3 Hz, 1H), 7.59 (m, 1H), 7.36 (m, 2H), 7.29 (m, 2H), 6.88 (m, 2H), 6.23 (bs, 1H), 5.19 (s, 2H); HPLC-MS (ESI) m/z 391 (M+H)+, 389 (M−H)−.

Workup

  1. extractionThe aq. phase was extracted with EtOAc (5 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-caebdfe6aaa04ba2aa47f1fe32740c6c
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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