Water → (2R)-2-[[2-Amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanol

HRID 1006510Notes

Reaction equation

HRID 1006510 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]([CH2:23][OH:24])[CH3:22].C(N(C(C)C)CC)(C)C.O>CN1CCCC1=O>[NH2:19][C:17]1[S:18][C:3]2[C:2]([NH:20][C@H:21]([CH3:22])[CH2:23][OH:24])=[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

6

Reactant 4

HCID 962WaterHCID 80308(R)-(-)-2-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine

Product 1

HCID 11857680(2R)-2-[[2-Amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-1-propanolYield 32%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

The product of example 1 step c) (25.0 g), D-Alaninol (12.3 g) and diisopropylethylamine (26.0 g) were diluted in N-methylpyrrolidinone (250 ml) and stirred at 100° C. for 24 h before cooling and pouring the reaction mixture into H2O (2.5 l). The precipitate was filtered and dried in vacuo before being preabsorped onto silica gel. Chromatography using EtOAc. 4% MeOH/EtOAc as eluents afforded the desired product as a yellow solid (9.0 g. 32%).

Workup

  1. temperaturebefore cooling
  2. filtrationThe precipitate was filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-fbe4f8d2d0b64ee7a036560f4cb4c28c
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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