3-[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propionic acid ethyl ester → 2-Chloro-9-cyclopentyl-7,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2280003Notes

Reaction equation

HRID 2280003 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:22])([CH3:21])[CH2:6][N:7]([C:13]1[C:18]([NH2:19])=[CH:17][N:16]=[C:15]([Cl:20])[N:14]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)C>CN(C=O)C>[Cl:20][C:15]1[N:16]=[CH:17][C:18]2[NH:19][C:4](=[O:3])[C:5]([CH3:22])([CH3:21])[CH2:6][N:7]([CH:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[C:13]=2[N:14]=1

Participants

3

Reactant 1

HCID 581539763-[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propionic acid ethyl ester

Product 1

HCID 581540122-Chloro-9-cyclopentyl-7,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propionic acid ethyl ester in DMF was heated to 140° C. for 2 hours. Solvent was evaporated in vacuo, ethyl acetate added, and the resulting solid filtered and dried under vacuum to give 2-Chloro-9-cyclopentyl-7,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Workup

  1. customSolvent was evaporated in vacuo, ethyl acetate
  2. additionadded
  3. filtrationthe resulting solid filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6032d443c8574b36a630baa6fa9efbb8
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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