Phenyl chloroformate → HCID 23043011, compound

HRID 2165707Notes

Reaction equation

[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15][CH3:16])[N:3]=1.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>>[CH3:9][C:6]1[C:7]([O:8][C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])=[C:2]([CH3:1])[N:3]=[C:4]([NH:10][CH2:11][CH:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:14][CH2:15][CH3:16])[N:5]=1

Participants

Reactant 2

HCID 15891Phenyl chloroformate

HCID 23043009HCID 23043009, compound

Product 1

HCID 23043011HCID 23043011, compound

Procedure

In a manner similar to that of the method of Example 2, the title compound was prepared from 0.76 g (2.6 mmol) of 4,6-dimethyl-5-hydroxy-2-phenylhexylaminopyrimidine and phenyl chloroformate (0.40 g, 2.6 mmol) to afford 0.74 g of product, mp: 76°-77° C. Mass spectrum m/e=419. NMR (CDCl3) delta: 7.4-6.9 (m, 10H); 4.99 (bs, 1H): 3.3 (q, 7, 4 Hz, 2H); 2.5 (t, 4 Hz, 2H); 2.3 (s, 6H): 1.8-1.1 (m, 8H). IR (CHCl3): 1780, 1583 cm-1. Anal. Calc'd for C25H29N3O3 : C, 71.57; H, 6.97: N, 10.02. Found: C, 71.51; H, 6.95; N, 10.09.

Sources & evidence

ORD record: ord-c12e83b6c5ad45f69eb7e93863741e4b
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04940712

Reaction notes

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