Ammonia → 7-[(3aS,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1054525Notes

Reaction equation

HRID 1054525 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23](Cl)[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1)=[N+:2]=[N-:3].[NH3:25]>CO>[N:1]([CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:25])[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866661147-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 867057457-[(3aS,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1 g, 2.87 mmol) in 7M NH3 in MeOH (0.41 ml) was heated to 100° C. in a sealed bomb for 48 hrs. The reaction mixture was concentrated under reduced pressure, and the crude material was purified by silica flash column chromatography, eluting with 100% DCM to 16% MeOH in DCM afford the title compound (527.5 mg, 56%) as a brown gum: MS (ESI+) for C15H19N7O2 m/z 330.5 [M+H]+, 352.0 [M+Na]+; LC purity 99% (UV), 100% (ELS) (ret. time, 1.34 min); 1H NMR (500 MHz, CDCl3) δ 8.31 (s, 1H), 7.03 (d, J=3.6 Hz, 1H), 6.37 (d, J=3.6 Hz, 1H), 5.08 (s, 2H), 4.98-5.03 (m, 1H), 4.98-5.03 (m, 1H), 4.91-4.98 (m, 1H), 4.61 (dd, J=7.1, 5.5 Hz, 1H), 4.61 (dd, J=7.1, 5.6 Hz, 1H), 3.57 (dd, J=5.9, 2.8 Hz, 2H), 2.15-2.36 (m, 1H), 2.36-2.61 (m, 2H), 1.58 (s, 3H), 1.32 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude material was purified by silica flash column chromatography
  3. washeluting with 100% DCM to 16% MeOH in DCM

Sources & evidence

ORD record
ord-80d1b23f2a6441ce9ef811ffcc0472f6
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

Loading…