Adenosine → HCID 178478407, compound

HRID 16623Notes

Reaction equation

HRID 16623 reaction equation
[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@H:20]1([NH:57][C:58]2[N:66]=[C:65]([Cl:67])[N:64]=[C:63]3[C:59]=2[N:60]=[CH:61][N:62]3[C@H:68]2[C@H:72](CC([O-])=O)[C@@H:71]([CH2:77][C:78]([O-])=[O:79])[C@H](C3N=NN(CC)N=3)O2)[CH2:25][CH2:24][C@H:23]([NH:26][C:27]2[N:35]=[C:34]([Cl:36])[N:33]=[C:32]3[C:28]=2[N:29]=[CH:30][N:31]3[C@H:37]2[C@H:41](CC([O-])=O)[C@@H:40]([CH2:46][C:47]([O-:49])=O)[C@H](C3N=NN(CC)N=3)O2)[CH2:22][CH2:21]1.N[C@H]1CC[C@H](N)CC1.C(N(C(C)C)CC)(C)C>C(O)CCC>[Cl:67][C:65]1[N:64]=[C:63]2[C:59]([N:60]=[CH:61][N:62]2[CH:68]2[CH2:72][CH2:71][CH2:77][CH2:78][O:79]2)=[C:58]([NH:57][C@H:20]2[CH2:25][CH2:24][C@H:23]([NH:26][C:27]3[N:35]=[C:34]([Cl:36])[N:33]=[C:32]4[C:28]=3[N:29]=[CH:30][N:31]4[CH:37]3[CH2:41][CH2:40][CH2:46][CH2:47][O:49]3)[CH2:22][CH2:21]2)[N:66]=1

Participants

6

Reactant 4

HCID 60961AdenosineHCID 81531DiisopropylethylamineHCID 178463183HCID 178463183, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478407HCID 178478407, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

A stirred suspension of 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (Intermediate 1 in WO03/080613) (1.14 kg) in n-butanol (1.7 L) was treated with trans-1,4-diaminocyclohexane (239.2 g) and di-iso-propylethylamine (2.5 L), then heated at 75° C. for 17 hours. The suspension was allowed to cool to ambient temperature, filtered, washed with n-butanol (2×2.3 L) and dried in vacuo at 60° C. to give the title compound (0.9 kg).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washwashed with n-butanol (2×2.3 L)
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-1907f8719254478fb587098d77c72465
Source dataset
uspto-grants-2010_06
Patent number
US07737126B2

Reaction notes

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