HCID 21883101, compound → HCID 135839363, compound

HRID 722247Notes

Reaction equation

HRID 722247 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([OH:9])[N:3]=1.C(O[Na])(C)=O.Br[CH:16]([CH:20]([CH3:22])[CH3:21])[CH2:17]C=O>CC#N.O>[NH2:1][C:2]1[NH:3][C:4](=[O:9])[C:5]2[C:16]([CH:20]([CH3:22])[CH3:21])=[CH:17][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 21883101HCID 21883101, compoundHCID 178418247HCID 178418247, compoundHCID 178507952HCID 178507952, compound

Product 1

HCID 135839363HCID 135839363, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 2,4-diamino-6-hydroxypyrimidine (6.68 g, 50 mmol), AcONa (8.3 g 100 mmol) and 3-bromo-4-methyl-pentanal (8.76 g, 50 mmol) in CH3CN (100 mL) and H2O (100 mL) was stirred at 25° C. overnight whereupon the starting materials gradually dissolved and the desired pyrrolo[2,3-d]pyrimidine precipitated. The precipitate was collected by filtration and washed with MeOH to give 2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (3.80 g, 40%). HPLC Rt: 4.408 min. 1H-NMR (DMSO-d6): δ 10.58 (s, 1H), 10.10 (s, 1H), 6.30 (s, 1H), 5.97 (s, 2H), 3.03 (7, 1H), 1.20 (s, 3H), 1.19 (s, 3H).

Workup

  1. dissolutiongradually dissolved
  2. customthe desired pyrrolo[2,3-d]pyrimidine precipitated
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-11678f69e34e413abee0979bf00c7305
Source dataset
uspto-grants-2006_11
Patent number
US07138402B2

Reaction notes

Loading…