Phenyl chloroformate → HCID 136350277, compound

HRID 1468791Notes

Reaction equation

HRID 1468791 reaction equation
C[N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]1.CN1[C:32](=O)[CH:31]=[C:30]([C:34]2[CH:39]=CN=CN=2)N=C1OC[C@H]1CCCN1.Cl[C:48](OC1C=CC=CC=1)=O>>[CH3:21][CH:16]([O:15][C:3]1[NH:2][C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=1)[C@H:17]1[CH2:48][CH2:20][CH2:19][N:18]1[C:22]([O:24][C:25]1[CH:39]=[CH:34][CH:30]=[CH:31][CH:32]=1)=[O:23]

Participants

4

Reactant 3

HCID 15891Phenyl chloroformateHCID 67977664HCID 67977664, compoundHCID 68160332HCID 68160332, compound

Product 1

HCID 136350277HCID 136350277, compound

Procedure

Phenyl (2R)-2-(1-methyl-6-oxo-1,6-dihydro-[4,4]bipyrimidinyl-2-yloxymethyl)pyrrolidine-1-carboxylate was prepared by the same manner as that of methyl 3-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidine-1-carboxylate except for utilizing (R)-1-methyl-2-(pyrrolidin-2-ylmethoxy)-1H-[4,4′]bipyrimidinyl-6-one (0.20 g, 0.70 mmol) instead of 1-methyl-2-(piperidine-3-yloxy)-1H-[4,4′]bipyrimidinyl-6-one and phenyl chloroformate (125 μl, 1.0 mmol) instead of methyl chloroformate. Phenyl (2R)-2-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxymethyl)pyrrolidine-1-carboxylate was isolated as a white solid (29 mg, 0.07 mmol, 10%).

Sources & evidence

ORD record
ord-11c7476ca0804006879dbe894772a418
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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