Water → 4-cinnamylthio-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidine

HRID 1155041Notes

Reaction equation

[CH2:1](Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[SH:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([C@@H:21]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]3[OH:23])[N:19]=[CH:20][C:13]=12.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([S:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([C@@H:21]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]3[OH:23])[N:19]=[CH:20][C:13]=12)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Cinnamyl bromide (3.04 g) was added to a stirred solution of 4-mercapto-1-β-D-ribofuranosylpyrazolo[3,4-d]-pyrimidine (4.0 g) and potassium carbonate (2.13 g) in N,N-dimethylformamide. The solution was heated (40° C. on an oil bath) for 2 hours. After cooling the reaction mixture was poured into water (0.6 l) and the resultant precipitate was collected and washed with water. The 4-cinnamylthio-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine so obtained was recrystallised from methanol, washed with water and dried (in vacuo at 55° C.), yield 3.2 g, m.p. 165°-166° C.

Workup

temperatureAfter cooling the reaction mixture
customthe resultant precipitate was collected
washwashed with water

Sources & evidence

ORD record: ord-919c8d364823459cb97edf759e26ab20
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04299824

Reaction notes

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