Sodium hydride → HCID 56643914, compound

HRID 595139Notes

Reaction equation

HRID 595139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][N:18]=3)=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:27]1[C:36]2[CH:35]=[C:34]3[O:37][CH2:38][O:39][C:33]3=[CH:32][C:31]=2[N:30]=[CH:29][N:28]=1>CN(C=O)C.CCOC(C)=O>[O:37]1[C:34]2=[CH:35][C:36]3[C:27]([O:23][C:20]4[CH:21]=[CH:22][C:17]([C:12]5[C:13](=[O:16])[N:14]([CH3:15])[C:9]([NH:8][C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)=[N:10][CH:11]=5)=[N:18][CH:19]=4)=[N:28][CH:29]=[N:30][C:31]=3[CH:32]=[C:33]2[O:39][CH2:38]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 149353678-Chloro-2H-[1,3]dioxolo[4,5-g]quinazolineHCID 68297825HCID 68297825, compound

Product 1

HCID 56643914HCID 56643914, compoundYield 113.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Fluoro-phenylamino)-5-(5-hydroxy-pyridin-2-yl)-3-methyl-3H-pyrimidin-4-one (2.18 g, 7 mmol) was dissolved in dry DMF (30 ml) to which was added 60% NaH (774 mg, 19.3 mmol). After the mixture was stirred at room temperature for several minutes, a suspension of 8-Chloro-[1,3]dioxolo[4,5-g]quinazoline (2.08 g, 6.7 mmol) in dry DMF (40 ml) was added. The reaction mixture was stirred at room temperature for 1-2 hrs, then diluted with EtOAc and washed with sat'd NaHCO3 (3×), H2O (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give crude title compound and further purification to yield product (3.68 g, 90%). 1HNMR (400 MHz, DMSO): 9.18 (s, 1H), 8.60 (m, 3H), 8.45 (d, 1H), 7.84 (s, 1H), 7.82 (m, 1H), 7.55 (m, 3H), 7.21 (m, 2H), 4.15 (s, 2H). LC/MS Calcd for (M+H)+485.4. found 485.9.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 1-2 hrs
  3. washwashed with sat'd NaHCO3 (3×), H2O (1×), sat'd NaCl (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give
  7. customcrude title compound and further purification

Sources & evidence

ORD record
ord-3962f5126f5e454b8adf06e282c8835e
Source dataset
uspto-grants-2016_01
Patent number
US09242991B2

Reaction notes

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