Dimethylformamide → HCID 9805331, compound

HRID 1823669Notes

Reaction equation

HRID 1823669 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[N:10]=[C:9]1[CH:19](Br)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[CH3:28][N:29]([CH:31]=[O:32])C>>[NH2:8][CH2:9][CH2:19][CH2:28][N:29]([CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[N:10]=1)[CH:20]([CH3:22])[CH3:21])[C:31](=[O:32])[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1.[N:24]([CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[N:10]=1)[CH:20]([CH3:22])[CH3:21])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86592839HCID 86592839, compound

Product 2

HCID 9805331HCID 9805331, compoundHCID 86592838HCID 86592838, compound

Procedure

Preparation of Formula 106 where R1 to R3 are H; R5 is Benzyl; R6 is i-Propyl; R6′ is H; W, X and Y are —C═; and Z is —N═: A mixture of 3-benzyl-2-(1-bromo-2-methyl-propyl)-3-H-pyrido[2,3-d]pyrimidin-4-one (9.603 mmol), NaN3 (1.25 g, 19.206 mmol) and DMF (25 mL) was stirred at 60 C overnight and concentrated under the reduced pressure. The residue was dissolved in dichloromethane, washed with water and brine, dried (Na2SO4) and concentrated. The desired product, 2-(1-azido-2-methyl-propyl)-3-benzyl-3-H-pyrido[2,3-d]pyrimidin-4-one, was obtained as a syrup which was taken on without further purification.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2aab548db13645fd8b35ddaeedbba041
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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