Methyl 3,3-dicyano-2,2-dimethylpropanoate → 4-Amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 536488Notes

Reaction equation

HRID 536488 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13](=[NH:15])[NH2:14])=[N:6]1.C[O:21][C:22](=O)[C:23]([CH3:30])([CH3:29])[CH:24]([C:27]#[N:28])[C:25]#[N:26]>C(O)(C)(C)C>[NH2:26][C:25]1[C:24]2[C:23]([CH3:30])([CH3:29])[C:22](=[O:21])[NH:28][C:27]=2[N:15]=[C:13]([C:7]2[C:8]3[CH2:12][CH2:11][CH2:10][C:9]=3[N:5]([CH2:4][C:3]3[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=3[F:1])[N:6]=2)[N:14]=1

Participants

4

Reactant 2

HCID 86657403Methyl 3,3-dicyano-2,2-dimethylpropanoateHCID 866920921-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidamide

Product 1

HCID 712856274-Amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

300 mg (1.15 mmol) of 1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidamide was dissolved with 2 ml tert.-butanol, 287 mg (1.38 mmol) of methyl-3,3-dicyano-2,2-dimethylpropanoate in 2 ml tert.-butanol and 181 mg (1.61 mmol) of potassium tert.-butylate was added and it was heated under reflux for 72 h. It was evaporated to dryness and the residue was mixed with water/isopropanol (v/v=3:1). The solid was filtered off and dried under high vacuum. 385 mg (80% of theor.) of the target compound was obtained.

Workup

  1. additionwas added
  2. temperatureit was heated
  3. temperatureunder reflux for 72 h
  4. customIt was evaporated to dryness
  5. additionthe residue was mixed with water/isopropanol (v/v=3:1)
  6. filtrationThe solid was filtered off
  7. customdried under high vacuum
  8. custom385 mg (80% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-0c6ed8d9bf3d4373956afa793a44d448
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

Loading…