Methanol → N-[2-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-5-[methoxycarbonyl]pyrimidin-4-yl]glycine

HRID 1871988Notes

Reaction equation

HRID 1871988 reaction equation
[CH3:1][C:2]1[CH:44]=[CH:43][C:5]2[CH:6]([C:16]3[C:17](=[O:42])[NH:18][C:19](=[O:41])[N:20]([C:22]4[N:27]=[C:26]([NH:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[C:25]([C:37]([O:39][CH3:40])=[O:38])=[CH:24][N:23]=4)[CH:21]=3)[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.CO>FC(F)(F)C(O)=O.ClCCl>[CH3:15][C:12]1[CH:13]=[CH:14][C:7]2[CH:6]([C:16]3[C:17](=[O:42])[NH:18][C:19](=[O:41])[N:20]([C:22]4[N:27]=[C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])[C:25]([C:37]([O:39][CH3:40])=[O:38])=[CH:24][N:23]=4)[CH:21]=3)[C:5]3[CH:43]=[CH:44][C:2]([CH3:1])=[CH:3][C:4]=3[CH:10]=[CH:9][C:8]=2[CH:11]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 867556552-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

Product 1

HCID 18689752N-[2-[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-5-[methoxycarbonyl]pyrimidin-4-yl]glycine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of the product of step (iii) (0.57 g) in trifluoroacetic acid (5 ml) and dichloromethane (10 ml) was stirred at room temperature for 5 hours. Methanol (30 ml) was added and the precipitate collected. The solid was dissolved in methanol and sodium hydroxide solution and the product precipitated out by addition of 2M HCl. Yield 0.26 g.

Workup

  1. customthe precipitate collected
  2. dissolutionThe solid was dissolved in methanol
  3. customsodium hydroxide solution and the product precipitated out by addition of 2M HCl

Sources & evidence

ORD record
ord-fddf329857be4daf8cbe19cc593f37e6
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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