Ammonia → HCID 19597398, compound

HRID 611544Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:24][CH:25]([OH:28])[CH2:26][OH:27])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:29]>O1CCOCC1>[NH2:29][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:24][CH:25]([OH:28])[CH2:26][OH:27])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3-[4-Chloro-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl]propan-1,2-diol (0.6 g) was dissolved in 1,4-dioxane (60 ml) and concentrated aqueous ammonia (60 ml, S.G. 0.880) was added. The mixture was stirred and heated at 120° C. for 18 hours in a pressure vessel. The mixture was evaporated under reduced pressure to give a residue which was partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed with water, dried and evaporated to give a residue which was purified by flash column chromatography on silica using ethyl acetate/industrial methylated spirit (9:1) as the mobile phase to give 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propan-1,2-diol. The structure was confirmed by 1H nmr and mass spectra.

Workup

customThe mixture was evaporated under reduced pressure
customto give a residue which
customwas partitioned between water and ethyl acetate
customThe ethyl acetate layer was separated
washwashed with water
customdried
customevaporated
customto give a residue which
customwas purified by flash column chromatography on silica

Sources & evidence

ORD record: ord-eb3441e6b61945878cbcdc57d9aa371a
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001839

Reaction notes

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