Bromine → HCID 9805331, compound

HRID 1823668Notes

Reaction equation

HRID 1823668 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[CH2:19][CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24]([O-:26])=O.[Na+].[Br:28]Br>C(O)(=O)C>[NH2:8][CH2:13][CH2:12][CH2:11][N:10]([CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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:24](=[O:26])[C:23]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1.[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:28])[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 71153931HCID 71153931, compound

Product 2

HCID 9805331HCID 9805331, compoundHCID 86592839HCID 86592839, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Preparation of Formula 105 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═: To a stirred, 40° C. mixture of 3-benzyl-2-isobutyl-3-H-pyrido[2,3-d]pyrimidin-4-one (2.82 g, 9.603 mmol), NaOAc (1.18 g, 14.41 mmol) and acetic acid (40 mL) was added bromine (2.31g, 14.41 mmol) dropwise. The reaction mixture was stirred at 40° C. for 1 h until complete consumption of the starting material was observed by TLC. The reaction mixture was poured into ice water (500 mL) and stirred at room temperature for 2 h. The precipitated product was isolated by filtration, washed with warm water to remove traces of acetic acid, and rinsed with a small amount of isopropanol. Drying under vacuum yielded the desired product, 3-benzyl-2-(1-bromo-2-methyl-propyl)-3-H-pyrido[2,3-d]pyrimidin-4-one, as a white solid which was taken on without further purification.

Workup

  1. stirringstirred at room temperature for 2 h
  2. customThe precipitated product was isolated by filtration
  3. washwashed with warm water
  4. customto remove traces of acetic acid
  5. washrinsed with a small amount of isopropanol
  6. customDrying under vacuum

Sources & evidence

ORD record
ord-67af807936f342d29543b8adba9b8a36
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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