1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 20491778, compound

HRID 434660Notes

Reaction equation

HRID 434660 reaction equation
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.O[CH2:26][C:27]1([CH3:31])[CH2:30][S:29][CH2:28]1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:26][C:27]2([CH3:31])[CH2:30][S:29][CH2:28]2)[CH:23]=1

Participants

5

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 15773547(3-Methylthietan-3-yl)methanol

Product 1

HCID 20491778HCID 20491778, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (2.72 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (789 mg) and 3-hydroxymethyl-3-methylthietane (1.000 g) in dry N,N-dimethylformamide (15 ml) under nitrogen and the mixture was then heated at 100° C. After 42.5 h the reaction mixture was evaporated and the resulting black residue was dissolved in ethyl acetate (300 ml), washed with water (3×70 ml), dried (MgSO4) and evaporated to a dark brown gum. Trituration of the gum with diethyl ether gave a pale brown solid which was crystallised from ethyl acetate to give cream crystals of the title pyrimidinone (110 mg), m.p. 200°-202° C., νmax (nujol) 1663, 1510 cm-1 (C=O), 1612, 1582 cm-1 (C=C, C=N).

Workup

  1. customAfter 42.5 h the reaction mixture was evaporated
  2. dissolutionthe resulting black residue was dissolved in ethyl acetate (300 ml)
  3. washwashed with water (3×70 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a dark brown gum
  6. customTrituration of the gum with diethyl ether gave a pale brown solid which
  7. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-1c6ae83c656f45f5bcbbda1be796c15a
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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