Water → (2R)-2-{[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino}pentan-1-ol

HRID 2422189Notes

Reaction equation

[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:29][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:31][OH:32].O>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([NH:29][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:31][OH:32])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (6.0 g, 19.4 mmol) was dissolved in NMP (30 mL). DIPEA (8.4 mL, 48.5 mmol) and 2-amino-(2R)-1-pentanol (3.5 g, 33.9 mmol) were added and the mixture was heated to 110° C. for 4 days. After cooling to room temperature, the mixture was poured into water (200 mL). The precipitated product was collected by filtration, washed with water and used in the next step without further purification (7.0 g, 97% yield).

Workup

temperatureAfter cooling to room temperature
filtrationThe precipitated product was collected by filtration
washwashed with water
customused in the next step without further purification (7.0 g, 97% yield)

Sources & evidence

ORD record: ord-98b11dfaa8a24451af0b590c9127fb64
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960395B2

Reaction notes

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