Water → 2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol

HRID 60534Notes

Reaction equation

CCN(C(C)C)C(C)C.[NH2:10][C@@H:11]([CH2:16][OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14].Cl[C:19]1[C:20]2[S:36][C:35]([NH2:37])=[N:34][C:21]=2[N:22]=[C:23]([S:25][C@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:27])[N:24]=1.O>CN1C(=O)CCC1>[NH2:37][C:35]1[S:36][C:20]2[C:19]([NH:10][CH:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:16][OH:17])=[N:24][C:23]([S:25][C@H:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH3:27])=[N:22][C:21]=2[N:34]=1

Participants

Conditions

Temperature: 120 °C

Procedure

DIPEA (400 mg, 3 mmol) and D-leucinol (400 mg, 3.4 mmol) were added to 7-chloro-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine (300 mg, 0.9 mmol) in NMP (6 mL) and the mixture was heated to 120° C. for 24 h. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried (MgSO4), evaporated and the residue was purified by flash column chromatography (EtOAc) to give the title compound (200 mg, 54% yield).

Workup

extractionextracted with ethyl acetate
dry with materialThe organic phase was dried (MgSO4)
customevaporated
customthe residue was purified by flash column chromatography (EtOAc)

Sources & evidence

ORD record: ord-6e89b2ba57dc4b95875c7e426c7ec9a5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440992B2

Reaction notes

Loading…