HCID 86592810, compound → HCID 12042145, compound

HRID 2216257Notes

Reaction equation

HRID 2216257 reaction equation
[Br:1]C1N(C2N=C(I)N=C(N)C=2N=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.[C:22]([O:25][C@@H:26]1[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@@H:29]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:28][C@@:27]1(Br)[N:40]1[C:49]2[N:48]=[C:47]([I:50])[N:46]=[C:44]([NH2:45])[C:43]=2[N:42]=[CH:41]1)(=[O:24])[CH3:23]>>[C:22]([O:25][C@@H:26]1[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@@H:29]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:28][C@H:27]1[N:40]1[C:49]2[N:48]=[C:47]([I:50])[N:46]=[C:44]([NH2:45])[C:43]=2[N:42]=[C:41]1[Br:1])(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 86592810HCID 86592810, compoundHCID 86592811HCID 86592811, compound

Product 1

HCID 12042145HCID 12042145, compound

Procedure

Amination of compound 5 or 6 to obtain the 8-alkylamino-2-iodoadenosines 7–10 was generally as follows: to 8-bromo-2-iodoadenosine (5) or 2′,3′,5′-tri-O-acetyl-2-iodo-bromoadenosine (6) (0.17 mmol) the appropriate alkylamine was added (excess) and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the product was crystallised from water.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product was crystallised from water

Sources & evidence

ORD record
ord-40d74305e5dc49679e259524a8413d0b
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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