Diisopropylethylamine → [(2R)-2-[[2-amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]propyl]carbamic acid, 1,1-dimethylethyl ester

HRID 1097353Notes

Reaction equation

HRID 1097353 reaction equation
Cl[C:2]1[C:3]2[S:18][C:17]([NH2:19])=[N:16][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=1.[NH2:20][C@H:21]([CH3:31])[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[NH2:19][C:17]1[S:18][C:3]2[C:2]([NH:20][C@H:21]([CH3:31])[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[N:7][C:6]([S:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:5][C:4]=2[N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amineHCID 45072491tert-butyl N-((2R)-2-aminopropyl)carbamate

Product 1

HCID 86635803[(2R)-2-[[2-amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]propyl]carbamic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

The product from example 1 step c) (2.0 g) and the product from example 25 step d) (1.3 g) in a solvent of NMP (10 ml) containing Hunigs base (3 ml) was heated at 110° C. for 10 hours. The mixture was evaporated to dryness and purified (SiO2, (1:1) dichloromethane:ethyl acetate as eluant) to give the subtitle compound (1.9 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified (SiO2, (1:1) dichloromethane:ethyl acetate as eluant)

Sources & evidence

ORD record
ord-dbecc4497a394e7ea65c8979894b0219
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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