Diisopropylethylamine → HCID 178463182, compound

HRID 1014957Notes

Reaction equation

HRID 1014957 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:38])=[N:25][C:26]=2[NH:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]1)(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[CH:54][N:55]2[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)=[C:51](Cl)[N:50]=1>C(O)(C)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:38])=[N:25][C:26]=2[NH:30][C@H:31]1[CH2:32][CH2:33][C@H:34]([NH:37][C:51]2[N:50]=[C:49]([Cl:48])[N:57]=[C:56]3[C:52]=2[N:53]=[CH:54][N:55]3[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)[CH2:35][CH2:36]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 178463186HCID 178463186, compound2×

Product 1

HCID 178463182HCID 178463182, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2R,3R,4R,5R)-2-{6-[(trans-4-Aminocyclohexyl)amino]-2-chloro-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate (Intermediate 4) (7.9 g) was dissolved in isopropanol (200 ml) and stirred at room temperature under nitrogen. N,N-diisopropylethylamine (10 ml) was added followed by 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (3.92 g). The mixture was stirred at 60° C. under nitrogen for 18 h. The reaction mixture was allowed to cool to room temperature and evaporated down in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was separated and the aqueous extracted twice with ethyl acetate. The organic phases were combined, dried (MgSO4), and evaporated down in vacuo to give the title compound (10.35 g). Used without purification.

Workup

  1. stirringThe mixture was stirred at 60° C. under nitrogen for 18 h
  2. temperatureto cool to room temperature
  3. customevaporated down in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. extractionthe aqueous extracted twice with ethyl acetate
  7. dry with materialdried (MgSO4)
  8. customevaporated down in vacuo

Sources & evidence

ORD record
ord-e601ac6747994d42b2b1e22fabd4c5c1
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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