Aluminium lithium hydride → HCID 22125152, compound

HRID 1858209Notes

Reaction equation

HRID 1858209 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[N:15]1[CH2:24][C:23]2[C:18](=[N:19][C:20]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][C:33](OCC)=[O:34])=[CH:28][CH:27]=3)=[N:21][CH:22]=2)[N:17]([CH3:38])[C:16]1=[O:39]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[N:15]1[CH2:24][C:23]2[C:18](=[N:19][C:20]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][OH:34])=[CH:28][CH:27]=3)=[N:21][CH:22]=2)[N:17]([CH3:38])[C:16]1=[O:39]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22125060HCID 22125060, compound

Product 1

HCID 22125152HCID 22125152, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of lithium aluminium hydride in anhydrous tetrahydrofuran (91 μl; 91 μmol) was added dropwise to a stirred solution of 40 mg (82 μmol) of ethyl 2-[4-[[3-(2,6-dichlorophenyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimido[4,5-d]pyrimidin-7-yl]amino]-phenyl]acetate in 4 ml of anhydrous tetrahydrofuran at 0° C. and the mixture was stirred for a further 90 minutes. The reaction was quenched with 10 ml of 2M sodium hydroxide and the mixture was extracted twice with 10 ml of ethyl acetate each time. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (2:1) for the elution. Product-containing fractions were evaporated to give 25 mg (68%) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-[4-(2-hydroxyethyl)anilino]-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 148-151° C.

Workup

  1. customThe reaction was quenched with 10 ml of 2M sodium hydroxide
  2. extractionthe mixture was extracted twice with 10 ml of ethyl acetate each time
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washfor the elution
  8. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-4f421048276c4c159bf2de4b746e7722
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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