Potassium tert-butoxide → 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 570520Notes

Reaction equation

HRID 570520 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:20]([CH:22]([C:30]#[N:31])[C:23]([CH3:29])([CH3:28])[C:24](OC)=[O:25])#[N:21].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[NH2:21][C:20]1[C:22]2[C:23]([CH3:29])([CH3:28])[C:24](=[O:25])[NH:31][C:30]=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

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 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 were admixed with 2 ml of tert-butanol, 287 mg (1.38 mmol) of methyl 3,3-dicyano-2,2-dimethylpropanoate dissolved in 2 ml of tert-butanol and 181 mg (1.61 mmol) of potassium tert-butoxide, and the mixture was heated under reflux for 72 h. The mixture was concentrated to dryness and the residue was stirred with water/isopropanol (v/v=3:1). The solid was filtered off and dried under high vacuum. 385 mg (80% of theory) of the target compound were obtained.

Workup

  1. temperatureunder reflux for 72 h
  2. concentrationThe mixture was concentrated to dryness
  3. filtrationThe solid was filtered off
  4. customdried under high vacuum
  5. custom385 mg (80% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-7186ea1e5bf54258a2965ec871bf8662
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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