Pyridine → 2-Bromo-9-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-beta-D-erythro-pentofuranosyl]-6-{[(dimethylamino)methylidene]amino}-9H-purine

HRID 2300956Notes

Reaction equation

HRID 2300956 reaction equation
[Br:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[CH2:12]2)=[C:4]([N:19]=[CH:20][N:21]([CH3:23])[CH3:22])[N:3]=1.N1C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:53]=[CH:52][C:35]([C:36](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:34][CH:33]=1>C(Cl)Cl.CO>[Br:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:16][C@H:15]([CH2:17][O:18][C:36]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[C:35]3[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:53][CH:52]=3)[C@@H:13]([OH:14])[CH2:12]2)=[C:4]([N:19]=[CH:20][N:21]([CH3:23])[CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 867587512-Bromo-9-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-{[(dimethylamino)methylidene]amino}-9H-purine

Product 1

HCID 867587522-Bromo-9-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-beta-D-erythro-pentofuranosyl]-6-{[(dimethylamino)methylidene]amino}-9H-purine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The compound was produced as described in example 9. The following were used: compound from example 17 (250 mg, 0.65 mmol), pyridine (2 ml), 4,4′-dimethoxytrityl chloride (330 mg, 0.98 mmol). FC cf. 9. Colourless solid (260 mg, 58%). TLC (CH2Cl2/MeOH, 9:1): Rf 0.37. 1H-NMR ((D6)DMSO): 2.23, 2.68 (2m, H—C(2′)); 3.01, 3.09 (2s, CH3—N); 3.57, 3.58 (2s, CH3O); 3.84 (m, H—C(4′)); 4.33 (m, H—C(3′)); 5.24 (d, J=4.5 Hz, HO—C(3′)); 6.22 (“t”, J=5.8 Hz, H—C(1′)); 6.6-7.2 (m, aromat. H); 8.21 (s, H—C(8)); 8.69 (s, H—C(N═)). Anal. calc. for C34H35BrN6O5 (687.59): C, 59.39; H, 5.13; N, 12.22; found: C, 59.46; H, 5.40; N, 12.09.

Workup

  1. customThe compound was produced

Sources & evidence

ORD record
ord-fa93a65be82e4689b00a9d331c5ed9e3
Source dataset
uspto-grants-2002_12
Patent number
US06498241B1

Reaction notes

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