1-Chloroethyl chloroformate → HCID 16063431, compound

HRID 1917261Notes

Reaction equation

HRID 1917261 reaction equation
Cl.C([N:9]1[CH2:18][CH2:17][C:16]2[C:15]([C:19]3[CH:23]=[C:22]([CH3:24])[S:21][CH:20]=3)=[N:14][C:13]([CH:25]([CH3:27])[CH3:26])=[N:12][C:11]=2[CH2:10]1)C1C=CC=CC=1.[Cl:28]C(OC(Cl)=O)C>ClCCCl>[ClH:28].[CH:25]([C:13]1[N:14]=[C:15]([C:19]2[CH:23]=[C:22]([CH3:24])[S:21][CH:20]=2)[C:16]2[CH2:17][CH2:18][NH:9][CH2:10][C:11]=2[N:12]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 16063313HCID 16063313, compound

Product 1

HCID 16063431HCID 16063431, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 7-benzyl-2-isopropyl-4-(5-methyl-thiophen-3-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine hydrochloride (0.133 g) in 1,2-dichloroethane (7 mL) was treated with 1-chloroethylchloroformate (0.105 mL). The mixture was heated at 95° C. for 16 h, concentrated, dissolved in MeOH, and heated at 50° C. for an additional 2 h. The mixture was concentrated and chromatographed on SiO2 (2 M NH3 in MeOH/CH2Cl2). MS (ESI): exact mass calcd. for C15H19N3S, 273.13; m/z found, 274.3 [M+H]+. 1H NMR (MeOH-d4): 7.81-7.80 (m, 1H), 7.36-7.35 (m, 1H), 4.42 (s, 2H), 3.55 (t, J=6.0, 2H), 3.25 (t, J=6.0, 2H), 3.19 (m, 1H), 2.55 (s, 3H), 1.35 (d, J=7.2, 6H).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in MeOH
  3. temperatureheated at 50° C. for an additional 2 h
  4. concentrationThe mixture was concentrated
  5. customchromatographed on SiO2 (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6fd4dfc5a4d44e27aba1d6df52219637
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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