Triphenylphosphine → HCID 89559199, compound

HRID 578748Notes

Reaction equation

HRID 578748 reaction equation
[C:1]1([CH:7]2[O:14][CH2:13][C@H:12]3[C@:10]([CH2:15]O)([CH2:11]3)[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[N:26]=[C:25]([NH2:27])[N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][NH:22]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CC1CCCO1>[Cl:17][C:18]1[N:26]=[C:25]([NH2:27])[N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:15][C@:10]12[CH2:11][C@H:12]1[CH2:13][O:14][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[O:8][CH2:9]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 71570849HCID 71570849, compoundHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 89559199HCID 89559199, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Procedure

In a reactor, a mixture of [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol (750 g, 3.4 mol) (5c), 6-chloro-9H-purin-2-amine (7c) (479 g, 2.8 mol) and triphenylphosphine (930 g, 3.5 mol) in 2-methyltetrahydrofuran (7.4 L) was stirred at room temperature for 30 minutes, and then heated to 65° C. (+/−5° C.). To this mixture was dosed a solution of DIAD (711 g, 3.5 mol) in 2-methyltetrahydrofuran (740 mL) over a period of 1 hour. The mixture was stirred during 1 hour at reflux and then allowed to cool to room temperature overnight. Solids were removed by filtration. The reactor was rinsed with 2-methyltetrahydrofuran (740 mL) and this liquid was used to wash the solids on the filter. The filtrate was submitted as such in the next step (6′).

Workup

  1. temperatureheated to 65° C. (+/−5° C.)
  2. customof 1 hour
  3. stirringThe mixture was stirred during 1 hour
  4. temperatureat reflux
  5. temperatureto cool to room temperature overnight
  6. customSolids were removed by filtration
  7. washThe reactor was rinsed with 2-methyltetrahydrofuran (740 mL)
  8. washto wash the solids on the filter

Sources & evidence

ORD record
ord-e09fd9e7bb684ca49461ccd0faf07a5f
Source dataset
uspto-grants-2015_05
Patent number
US09040699B2

Reaction notes

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