R-(-)-1,2-Propanediol → (2R)-2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propan-1-ol

HRID 1926892Notes

Reaction equation

HRID 1926892 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.ClC1C2C(C3C=CC(CC)=CC=3)=C(C3C=CC=CC=3)OC=2N=CN=1.[CH2:49]([OH:53])[C@@H:50]([OH:52])[CH3:51].C(O)[C@H](O)C>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([O:52][C@H:50]([CH3:51])[CH2:49][OH:53])=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 259994R-(-)-1,2-PropanediolHCID 439846(S)-propane-1,2-diolHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidineHCID 580168974-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 58016907(2R)-2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propan-1-ol

Procedure

Production of the compounds listed in the following table is analogous to the synthesis described above. It starts correspondingly from 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]-pyrimidine or from 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine and uses (2S)-propane-1,2-diol or (2R)-propane-1,2-diol respectively:

Sources & evidence

ORD record
ord-d214f2471ab2466a8aa6de20bb654620
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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