2,6-Di(methoxyacetamido)-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine → 2-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine

HRID 487718Notes

Reaction equation

COCC([NH:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:17]2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:9]([NH:46]C(=O)COC)[N:8]=1)=O.C[O-].[Na+]>CO>[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:17]2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:9]([NH2:46])[N:8]=1

Participants

Conditions

Temperature: 61 °C

Procedure

The protected 2,6-di(methoxyacetamido)purine (IV) (1.55 kg, 2.20 mol) was dissolved in methanol (3.6 L) with stirring and warmed to 46°-48° C. A solution of sodium methoxide (30 g, 95%, 0.55 mol, in 250 mL methanol) was added and the solution was warmed to 61° C. The reaction was completed in about 1 hour (tlc) at which time the product started to precipitate. The mixture was allowed to cool to 30° C. and then refrigerated overnight. The product was collected, washed with ice-cold methanol (800 mL) and air-dried to give the title compound (V) 823 g (68%), mp 60°-62° C.

Workup

temperaturewarmed to 46°-48° C
customto precipitate
temperatureto cool to 30° C.
customrefrigerated overnight
customThe product was collected
washwashed with ice-cold methanol (800 mL)
customair-dried

Sources & evidence

ORD record: ord-0b589934e0d14b6d8fcf00f54e5f540f
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05296589

Reaction notes

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