Triphenylphosphine → HCID 66780559, compound

HRID 1958065Notes

Reaction equation

HRID 1958065 reaction equation
[N:1]([CH:4]([C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[CH3:20])[C:10]2[N:21]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:23][C:9]=2[C:8](=[O:30])[N:7]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH:4]([C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[CH3:20])[C:10]2[N:21]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:23][C:9]=2[C:8](=[O:30])[N:7]=1)[CH3:5]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86662602HCID 86662602, compound

Product 1

HCID 66780559HCID 66780559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-(1-azidoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (48 mg, 0.108 mmol) in Tetrahydrofuran (THF) (1 mL) was added resin-bound triphenylphosphine (28.2 mg, 0.108 mmol) and the mixture was stirred at 60° C. overnight. The reaction was then quenched with water and stirred at 60° C. for 1 hr. The resin was removed by filtration and the filtrate was then extracted with dichloromethane. The organic solution was dried over sodium sulfate, filtered, and concentrated to provide the desired product as a brown solid. This crude material was purified on a silica gel column eluting with chloroform/(a solution of 2M ammonia in methanol) (99:1). The fractions containing product were combined, then concentrated to provide 5-(1-aminoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl) [1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (19 mg, 0.045 mmol, 42.0% yield). LC/MS m/z MH+=420 (theoretical), found=420.1, 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.44 (d, J=6.82 Hz, 3H) 2.48 (s, 3H) 3.53-3.63 (m, 4H) 3.72-3.85 (m, 5H) 4.02 (br. s., 1H) 5.42 (d, J=17.68 Hz, 1H) 5.78 (d, J=17.18 Hz, 1H) 6.49 (d, J=7.83 Hz, 1H) 7.07 (t, J=7.96 Hz, 1H) 7.34 (d, J=7.83 Hz, 1H)

Workup

  1. customThe reaction was then quenched with water
  2. stirringstirred at 60° C. for 1 hr
  3. customThe resin was removed by filtration
  4. extractionthe filtrate was then extracted with dichloromethane
  5. dry with materialThe organic solution was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1fdfa6e06b048889767de9d5471613f
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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