Diiodomethane → HCID 86705365, compound

HRID 536492Notes

Reaction equation

HRID 536492 reaction equation
N[C:2]1[C:3]2[C:27]([CH3:29])([CH3:28])[C:26](=[O:30])[NH:25][C:4]=2[N:5]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:11]3=[C:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:7]=1.N(OCCC(C)C)=O.[I:39]CI>CN1C(=O)CCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][C:10]1[N:9]=[C:8]([C:6]2[N:7]=[C:2]([I:39])[C:3]3[C:27]([CH3:28])([CH3:29])[C:26](=[O:30])[NH:25][C:4]=3[N:5]=2)[N:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:11]=12

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl Nitrite2×HCID 71285432HCID 71285432, compound

Product 1

HCID 86705365HCID 86705365, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

1.500 g (3.35 mmol) of 4-amino-2-[8-(2-fluorobenzyl)imidazo[1,5-a]pyrimidin-6-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one was suspended in 6.00 ml (44.56 mmol) of isopentyl nitrite and 4.00 ml (49.66 mmol) of diiodomethane and it was stirred for 2d at 85° C. 4.00 ml isopentyl nitrite and 5 ml NMP were added and the solution was stirred for 4 h at 85° C. The mixture was concentrated by evaporation in the rotary evaporator except the NMP and was purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→100:0). 928 mg (purity 69%, 37% of theor.) of the target compound was obtained.

Workup

  1. concentrationThe mixture was concentrated by evaporation in the rotary evaporator except the NMP
  2. customwas purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→100:0)
  3. custom928 mg (purity 69%, 37% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-7ad6afdde597467190141690b5671b1f
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

Loading…