Formic Acid → methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

HRID 2175926Notes

Reaction equation

HRID 2175926 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[CH:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][C:13]=2[N:14]=1.C(O)=O>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:8][C:9]1[N:10]=[CH:11][C:12]2[CH:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][C:13]=2[N:14]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 86727111methyl 2-amino-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

Product 1

HCID 86727113methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (3.20 mL, 23.0 mmol) was added to a solution of methyl 2-amino-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate (2.11 g, 9.27 mmol) in dioxane (42 mL) followed by formic acid (0.89 mL, 22.28 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (660 mg, 0.902 mmol). The reaction mixture was heated at 100° C. in a sealed tube overnight. The solvent was evaporated. The residue was purified by chromatography on silica (220 g+125 g cartridges) using CH2Cl2: MeOH 95:5 to afford the title compound which was used without further purification in the next step.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by chromatography on silica (220 g+125 g cartridges)

Sources & evidence

ORD record
ord-acca13ddadf641efb56ded7d6af76304
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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